feat(desktop): enrich the DM chat composer + message UX

Brings the desktop DM experience up to par with a modern chat client,
reusing existing commons/quartz infrastructure throughout.

Composer:
- Emoji picker (org.kodein.emoji, MIT) with search; unicode + NIP-30
  custom-emoji ":shortcode:" autocomplete in one strip
- @mention autocomplete (avatar + display name) inserting nostr:npub
- Reply-quoting: composer bar + a quoted chip on reply bubbles that taps
  to scroll-and-highlight the original (bounce + flash)
- Per-message image quality selector; send-in-progress spinner

Rendering:
- DM bubbles render rich text (mentions resolve to names; image/GIF/
  custom-emoji inline) instead of raw text

GIF search (Nostr-native, no third-party API):
- Query NIP-94 kind-1063 GIF metadata from a configurable relay list
  (nos.lol + relay.damus.io), dedup + client-side filter, animated preview

Uploads / privacy:
- Encrypted DM files upload as opaque application/octet-stream by default
  so the media server can't learn the media type; optional "Reveal media
  type" toggle for strict servers. Only reencode jpg/png/webp; GIF/video/
  AVIF/HEIC pass through. Actionable errors for servers that reject
  private uploads
- Reply/glyph: add a real Reply icon to the Material Symbols subset

Robustness:
- Preserve Messages state (selected room, draft, attachments) across the
  device lock by hoisting it above the lock gate
- Thread the send so the composer always clears and errors surface

Adds unit tests for the GIF merge/filter and caret insertion.

Co-Authored-By: Claude Opus 4.8 (1M context) <noreply@anthropic.com>

commons/src/commonMain/kotlin/com/vitorpamplona/amethyst/commons/icons/symbols/MaterialSymbols.kt

@@ -209,6 +209,7 @@ object MaterialSymbols {
     val RemoveCircleOutline = MaterialSymbol("\uF08F")
     val RemoveDone = MaterialSymbol("\uE9D3")
     val Replay = MaterialSymbol("\uE042")
+    val Reply = MaterialSymbol("\uE15E")
     val Report = MaterialSymbol("\uF052")
     val Restaurant = MaterialSymbol("\uE56C")
     val Save = MaterialSymbol("\uE161")

commons/src/commonMain/kotlin/com/vitorpamplona/amethyst/commons/viewmodels/ChatNewMessageState.kt

@@ -25,6 +25,7 @@ import androidx.compose.ui.text.input.TextFieldValue
 import com.vitorpamplona.amethyst.commons.model.IAccount
 import com.vitorpamplona.amethyst.commons.model.Note
 import com.vitorpamplona.amethyst.commons.model.cache.ICacheProvider
+import com.vitorpamplona.amethyst.commons.model.nip30CustomEmojis.EmojiPackState
 import com.vitorpamplona.quartz.nip01Core.core.HexKey
 import com.vitorpamplona.quartz.nip01Core.relay.normalizer.NormalizedRelayUrl
 import com.vitorpamplona.quartz.nip01Core.tags.hashtags.hashtags
@@ -38,6 +39,7 @@ import com.vitorpamplona.quartz.nip17Dm.messages.ChatMessageEvent
 import com.vitorpamplona.quartz.nip17Dm.messages.changeSubject
 import com.vitorpamplona.quartz.nip18Reposts.quotes.quotes
 import com.vitorpamplona.quartz.nip19Bech32.toNpub
+import com.vitorpamplona.quartz.nip30CustomEmoji.emojis
 import com.vitorpamplona.quartz.utils.Hex
 import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.flow.MutableStateFlow
@@ -72,6 +74,13 @@ class ChatNewMessageState(
      * cache-only strict check.
      */
     private val dmInboxResolver: (suspend (HexKey) -> List<NormalizedRelayUrl>?)? = null,
+    /**
+     * Optional NIP-30 custom-emoji pack state. When provided, [sendNip17]
+     * resolves any `:shortcode:` in the outgoing message against the account's
+     * selected packs and attaches the matching `emoji` tags so recipients render
+     * the custom emojis. Null (default) → no custom-emoji tagging.
+     */
+    private val emojiPacks: EmojiPackState? = null,
 ) {
     private val _message = MutableStateFlow(TextFieldValue(""))
     val message: StateFlow<TextFieldValue> = _message.asStateFlow()
@@ -208,6 +217,7 @@ class ChatNewMessageState(
 
         val replyHint = _replyTo.value?.toEventHint<BaseDMGroupEvent>()
         val subjectText = _subject.value.text.ifBlank { null }
+        val emojiTags = emojiPacks?.findEmojiTags(messageText)?.takeIf { it.isNotEmpty() }
 
         val template =
             if (replyHint == null) {
@@ -216,6 +226,7 @@ class ChatNewMessageState(
                     hashtags(findHashtags(messageText))
                     references(findURLs(messageText))
                     quotes(findNostrEventUris(messageText))
+                    emojiTags?.let { emojis(it) }
                 }
             } else {
                 ChatMessageEvent.reply(messageText, replyHint) {
@@ -223,6 +234,7 @@ class ChatNewMessageState(
                     hashtags(findHashtags(messageText))
                     references(findURLs(messageText))
                     quotes(findNostrEventUris(messageText))
+                    emojiTags?.let { emojis(it) }
                 }
             }
 

commons/src/jvmMain/kotlin/com/vitorpamplona/amethyst/commons/service/upload/UploadOrchestrator.kt

@@ -161,41 +161,94 @@ class UploadOrchestrator(
         cipher: AESGCM,
         serverBaseUrl: String,
         signer: NostrSigner,
+        // Defaults preserve the prior behaviour exactly (no reencode, no EXIF
+        // strip → encrypt raw bytes) for existing Android/CLI callers. Only
+        // callers that opt in (e.g. Desktop DMs) change what leaves the machine.
+        stripExif: Boolean = false,
+        quality: CompressionQuality? = null,
+        // When false (default) the encrypted blob is uploaded as opaque
+        // application/octet-stream so the server can't learn the media type.
+        // When true it's uploaded with the real media type — less private, but
+        // required by strict Blossom servers that reject octet-stream (HTTP 415).
+        declareRealMimeType: Boolean = false,
     ): EncryptedUploadResult {
-        // 1. Compute pre-encryption metadata (dimensions, blurhash, mime, originalHash)
-        val metadata = MediaMetadataReader.compute(file)
+        var reencodedTemp: File? = null
+        var strippedTemp: File? = null
+        try {
+            // 1. Re-encode (or pass-through) BEFORE encrypting, mirroring [upload].
+            //    quality == null → pass-through (preserves prior DM behaviour, and
+            //    the CLI/Android callers). ImageReencoder itself passes animated
+            //    GIFs through byte-identical, so GIF DMs stay animated.
+            val reencode =
+                when {
+                    quality == null -> ReencodeResult.PassThrough(ImageReencoder.PassReason.BypassByUser)
+                    else -> ImageReencoder.reencode(file, quality)
+                }
+            val afterReencode =
+                when (reencode) {
+                    is ReencodeResult.Reencoded -> reencode.file.also { reencodedTemp = it }
+                    is ReencodeResult.PassThrough -> file
+                }
 
-        // 2. Read file bytes and encrypt
-        val plaintext = file.readBytes()
-        val encrypted = cipher.encrypt(plaintext)
+            // 2. Strip EXIF only when shipping the original (re-encode wipes it).
+            val finalFile =
+                if (stripExif && reencode is ReencodeResult.PassThrough) {
+                    val stripped = MediaCompressor.stripExif(afterReencode)
+                    if (stripped != afterReencode) strippedTemp = stripped
+                    stripped
+                } else {
+                    afterReencode
+                }
 
-        // 3. Compute SHA256 of ENCRYPTED blob (not plaintext)
-        val encryptedHash = sha256(encrypted).toHexKey()
-        val encryptedSize = encrypted.size
+            // 3. Compute pre-encryption metadata on the bytes that get encrypted
+            //    (dimensions, blurhash, mime, originalHash of the final plaintext).
+            val metadata = MediaMetadataReader.compute(finalFile)
 
-        // 4. Create Blossom auth with encrypted hash and size
-        val authHeader =
-            BlossomAuth.createUploadAuth(
-                hash = encryptedHash,
-                size = encryptedSize.toLong(),
-                alt = "Encrypted upload",
-                signer = signer,
+            // 4. Read final bytes and encrypt
+            val plaintext = finalFile.readBytes()
+            val encrypted = cipher.encrypt(plaintext)
+
+            // 5. Compute SHA256 of ENCRYPTED blob (not plaintext)
+            val encryptedHash = sha256(encrypted).toHexKey()
+            val encryptedSize = encrypted.size
+
+            // 6. Create Blossom auth with encrypted hash and size
+            val authHeader =
+                BlossomAuth.createUploadAuth(
+                    hash = encryptedHash,
+                    size = encryptedSize.toLong(),
+                    alt = "Encrypted upload",
+                    signer = signer,
+                )
+
+            // 7. Upload the encrypted blob. Default: declare
+            //    application/octet-stream so the server can't learn whether a
+            //    private attachment is an image, video, voice note, etc. — this
+            //    needs a server that accepts opaque blobs (e.g. nostr.download).
+            //    Callers may opt into [declareRealMimeType] to declare the real
+            //    type instead, so strict servers that reject octet-stream (HTTP
+            //    415) also work, at the cost of leaking the media category.
+            val uploadContentType =
+                if (declareRealMimeType) metadata.mimeType else "application/octet-stream"
+            val result =
+                client.upload(
+                    bytes = encrypted,
+                    contentType = uploadContentType,
+                    serverBaseUrl = serverBaseUrl,
+                    authHeader = authHeader,
+                )
+
+            return EncryptedUploadResult(
+                blossom = result,
+                metadata = metadata,
+                encryptedHash = encryptedHash,
+                encryptedSize = encryptedSize,
             )
-
-        // 5. Upload encrypted blob as opaque binary
-        val result =
-            client.upload(
-                bytes = encrypted,
-                contentType = "application/octet-stream",
-                serverBaseUrl = serverBaseUrl,
-                authHeader = authHeader,
-            )
-
-        return EncryptedUploadResult(
-            blossom = result,
-            metadata = metadata,
-            encryptedHash = encryptedHash,
-            encryptedSize = encryptedSize,
-        )
+        } finally {
+            withContext(NonCancellable) {
+                strippedTemp?.deleteOrWarn("UploadOrchestrator", "encrypted stripped temp")
+                reencodedTemp?.deleteOrWarn("UploadOrchestrator", "encrypted reencoded temp")
+            }
+        }
     }
 }

desktopApp/build.gradle.kts

@@ -57,6 +57,9 @@ dependencies {
     implementation(libs.coil.okhttp)
     implementation(libs.coil.svg)
 
+    // Unicode emoji picker (Kodein Emoji.kt — MIT; offline system-font rendering on desktop)
+    implementation(libs.kodein.emoji.compose.m3)
+
     // Video / audio playback — MIT, OS-native backends (MF / AVFoundation / GStreamer)
     // composemediaplayer 0.10.0 leaks kotlinx-coroutines-test as a *runtime* dependency
     // in its published POM. That jar ships a META-INF/services registration for

desktopApp/plans/2026-08-18-chat-composer-enrichment-manual-testing.md

@@ -0,0 +1,60 @@
+# Desktop Chat Composer Enrichment — Manual Testing Sheet
+
+**Branch:** `feat/desktop-chat-composer-enrichment`
+**Run:** `./gradlew :desktopApp:run`, log in with an account that has NIP-17 DMs, open **Messages**, select a conversation.
+
+Legend: ☐ untested · ✅ pass · ❌ fail (note issue)
+
+## P0 — TextFieldValue composer (foundation)
+- ☐ Type text; move the caret with arrow keys/click mid-word — cursor position holds.
+- ☐ Cmd/Ctrl+Enter sends; Enter alone inserts a newline.
+
+## P1 — Reply-quoting
+- ☐ Hover a message → quote (❝) icon appears; click it → a reply bar shows the quoted author + snippet above the input.
+- ☐ Send → recipient sees a threaded reply (reply marker present).
+- ☐ Click the ✕ on the reply bar → reply target cleared; next send is a normal message.
+- ☐ Reply, then send → reply bar auto-clears after send.
+
+## P2 — Emoji picker
+- ☐ Click the 🙂 (EmojiEmotions) button → grid opens.
+- ☐ Search "fire" → grid filters; click 🔥 → inserted at the caret (not appended blindly).
+- ☐ Insert an emoji mid-word → lands at the cursor, text splits correctly.
+- ☐ Works offline (disable network) — emojis still render via system font.
+
+## P3 — NIP-30 custom emoji
+- ☐ (Requires an emoji pack selected on the account.) Type `:` + a prefix → suggestion strip shows matching pack emojis with images.
+- ☐ Click one → `:shortcode:` inserted at the caret.
+- ☐ Send → recipient renders the custom emoji (event carries `emoji` tags).
+- ☐ No pack selected → no strip appears, no errors.
+
+## P4 — @mention
+- ☐ Type `@` + a name prefix → dropdown of matching cached users.
+- ☐ Click one → `nostr:npub…` inserted (with trailing space); dropdown closes.
+- ☐ Recipient/link resolves to the mentioned profile.
+- ☐ `#hashtag` — typing `#tag` still tags the note on send (no dropdown; deferred — no hashtag index).
+
+## P5 — Per-message image quality
+- ☐ Attach a JPEG/PNG → a "Quality:" chip appears above the input.
+- ☐ Send at **Low** vs **Uncompressed** → recipient's received file is visibly smaller at Low (check dimensions/size).
+- ☐ Attach an animated GIF → sends animated (byte-identical pass-through), quality chip hidden for GIF-only.
+- ☐ Quality override resets to the default after each send.
+- ☐ EXIF: a photo with GPS EXIF sent at pass-through has EXIF stripped (desktop opts in).
+
+## P6 — Nostr-native GIF search
+- ☐ Click **GIF** → panel opens, loads recent GIFs from `relay.gifbuddy.lol`.
+- ☐ Search "cat" → grid updates (debounced ~350ms).
+- ☐ Click a GIF → its URL inserted into the message; send → renders inline/animated for the recipient.
+- ☐ Add a second relay via `DesktopPreferences.gifRelays` → results merge, deduped by URL.
+- ☐ Point at an unreachable relay → panel degrades to empty/"No GIFs found", no crash, composer still usable.
+
+## Cross-feature integration
+1. ☐ One message mixing a unicode emoji + `:customshortcode:` + `@mention` + `#tag` → sends; recipient renders all; event carries `emoji`, `p`, `t` tags.
+2. ☐ Reply to a message and send → reply preserved; `clear()` resets the whole composer.
+3. ☐ Switch rooms mid-typing (with an open suggestion) → no stale dropdown / no cross-room leakage.
+4. ☐ Compact (narrow) and split (wide) layouts both wire the composer correctly.
+
+## Regression
+- ☐ Plain-text send still works.
+- ☐ File attach + drag-and-drop still work.
+- ☐ Quick-reaction bar on messages still works.
+</content>

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/DesktopPreferences.kt

@@ -93,6 +93,31 @@ object DesktopPreferences {
             prefs.put(KEY_PINNED_NAV_ITEMS, value)
         }
 
+    private const val KEY_ENCRYPTED_MEDIA_REAL_TYPE = "encrypted_media_real_type"
+
+    // When false (default), encrypted DM file uploads declare
+    // application/octet-stream so the Blossom server can't learn the media type
+    // (image/video/voice/…). When true, they declare the real media type — less
+    // private, but works with strict servers (blossom.band, primal, …) that
+    // reject octet-stream. Off by default = privacy-preserving.
+    var encryptedMediaRealType: Boolean
+        get() = prefs.getBoolean(KEY_ENCRYPTED_MEDIA_REAL_TYPE, false)
+        set(value) = prefs.putBoolean(KEY_ENCRYPTED_MEDIA_REAL_TYPE, value)
+
+    private const val KEY_GIF_RELAYS = "gif_relays"
+
+    // Nostr-native GIF search: relays that index NIP-94 (kind 1063) GIF metadata
+    // (GIF Buddy publishes here). Its dedicated relay.gifbuddy.lol is dead (404),
+    // so default to general relays that carry these events. User-editable; merged.
+    private const val DEFAULT_GIF_RELAY = "wss://nos.lol,wss://relay.damus.io"
+
+    var gifRelays: List<String>
+        get() {
+            val raw = prefs.get(KEY_GIF_RELAYS, DEFAULT_GIF_RELAY)
+            return if (raw.isBlank()) emptyList() else raw.split(",").map { it.trim() }.filter { it.isNotEmpty() }
+        }
+        set(value) = prefs.put(KEY_GIF_RELAYS, value.joinToString(","))
+
     private const val KEY_SIDEBAR_COLLAPSED = "sidebar_collapsed"
 
     var sidebarCollapsed: Boolean

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ImageCompressionStore.kt

@@ -45,6 +45,12 @@ object ImageCompressionStore {
     private val _stripExif = MutableStateFlow(DesktopPreferences.imageStripExif)
     val stripExif: StateFlow<Boolean> = _stripExif.asStateFlow()
 
+    // When true, encrypted DM file uploads declare the real media type instead of
+    // application/octet-stream — less private, but works with strict Blossom
+    // servers that reject octet-stream. Off by default (privacy-preserving).
+    private val _encryptedMediaRealType = MutableStateFlow(DesktopPreferences.encryptedMediaRealType)
+    val encryptedMediaRealType: StateFlow<Boolean> = _encryptedMediaRealType.asStateFlow()
+
     fun setQuality(quality: CompressionQuality) {
         _quality.value = quality
         DesktopPreferences.imageQualityRaw = quality.name
@@ -54,4 +60,9 @@ object ImageCompressionStore {
         _stripExif.value = value
         DesktopPreferences.imageStripExif = value
     }
+
+    fun setEncryptedMediaRealType(value: Boolean) {
+        _encryptedMediaRealType.value = value
+        DesktopPreferences.encryptedMediaRealType = value
+    }
 }

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/ChatPane.kt

@@ -20,7 +20,14 @@
  */
 package com.vitorpamplona.amethyst.desktop.ui.chats
 
+import androidx.compose.animation.animateColorAsState
+import androidx.compose.animation.core.Spring
+import androidx.compose.animation.core.animateFloatAsState
+import androidx.compose.animation.core.spring
+import androidx.compose.animation.core.tween
+import androidx.compose.foundation.background
 import androidx.compose.foundation.border
+import androidx.compose.foundation.clickable
 import androidx.compose.foundation.draganddrop.dragAndDropTarget
 import androidx.compose.foundation.layout.Arrangement
 import androidx.compose.foundation.layout.Box
@@ -38,8 +45,8 @@ import androidx.compose.foundation.lazy.LazyColumn
 import androidx.compose.foundation.lazy.items
 import androidx.compose.foundation.lazy.rememberLazyListState
 import androidx.compose.foundation.shape.RoundedCornerShape
-import androidx.compose.foundation.text.selection.SelectionContainer
 import androidx.compose.material3.AlertDialog
+import androidx.compose.material3.CircularProgressIndicator
 import androidx.compose.material3.HorizontalDivider
 import androidx.compose.material3.IconButton
 import androidx.compose.material3.MaterialTheme
@@ -53,17 +60,20 @@ import androidx.compose.runtime.Composable
 import androidx.compose.runtime.LaunchedEffect
 import androidx.compose.runtime.collectAsState
 import androidx.compose.runtime.getValue
-import androidx.compose.runtime.mutableStateListOf
 import androidx.compose.runtime.mutableStateOf
 import androidx.compose.runtime.remember
 import androidx.compose.runtime.rememberCoroutineScope
 import androidx.compose.runtime.setValue
+import androidx.compose.runtime.snapshots.SnapshotStateList
 import androidx.compose.ui.Alignment
 import androidx.compose.ui.ExperimentalComposeUiApi
 import androidx.compose.ui.Modifier
 import androidx.compose.ui.draganddrop.DragAndDropEvent
 import androidx.compose.ui.draganddrop.DragAndDropTarget
 import androidx.compose.ui.draw.alpha
+import androidx.compose.ui.draw.clip
+import androidx.compose.ui.graphics.Color
+import androidx.compose.ui.graphics.graphicsLayer
 import androidx.compose.ui.input.key.Key
 import androidx.compose.ui.input.key.KeyEventType
 import androidx.compose.ui.input.key.isCtrlPressed
@@ -73,6 +83,8 @@ import androidx.compose.ui.input.key.onPreviewKeyEvent
 import androidx.compose.ui.input.key.type
 import androidx.compose.ui.input.pointer.PointerEventType
 import androidx.compose.ui.input.pointer.onPointerEvent
+import androidx.compose.ui.text.TextRange
+import androidx.compose.ui.text.input.TextFieldValue
 import androidx.compose.ui.text.style.TextOverflow
 import androidx.compose.ui.unit.IntOffset
 import androidx.compose.ui.unit.dp
@@ -80,19 +92,39 @@ import androidx.compose.ui.window.Popup
 import androidx.compose.ui.window.PopupProperties
 import com.vitorpamplona.amethyst.commons.icons.symbols.Icon
 import com.vitorpamplona.amethyst.commons.icons.symbols.MaterialSymbols
+import com.vitorpamplona.amethyst.commons.model.EmptyTagList
 import com.vitorpamplona.amethyst.commons.model.IAccount
 import com.vitorpamplona.amethyst.commons.model.Note
+import com.vitorpamplona.amethyst.commons.model.User
 import com.vitorpamplona.amethyst.commons.model.cache.ICacheProvider
+import com.vitorpamplona.amethyst.commons.model.nip30CustomEmojis.EmojiPackState
+import com.vitorpamplona.amethyst.commons.model.toImmutableListOfLists
+import com.vitorpamplona.amethyst.commons.richtext.CachedRichTextParser
+import com.vitorpamplona.amethyst.commons.service.upload.CompressionQuality
 import com.vitorpamplona.amethyst.commons.service.upload.UploadOrchestrator
 import com.vitorpamplona.amethyst.commons.ui.components.LoadingState
 import com.vitorpamplona.amethyst.commons.ui.feeds.FeedState
+import com.vitorpamplona.amethyst.commons.ui.text.currentWord
+import com.vitorpamplona.amethyst.commons.ui.text.insertUrlAtCursor
+import com.vitorpamplona.amethyst.commons.ui.text.replaceCurrentWord
 import com.vitorpamplona.amethyst.commons.viewmodels.ChatNewMessageState
 import com.vitorpamplona.amethyst.commons.viewmodels.ChatroomFeedViewModel
+import com.vitorpamplona.amethyst.desktop.ImageCompressionStore
+import com.vitorpamplona.amethyst.desktop.cache.DesktopLocalCache
 import com.vitorpamplona.amethyst.desktop.model.DEFAULT_BLOSSOM_SERVER
 import com.vitorpamplona.amethyst.desktop.ui.LocalBlossomServers
+import com.vitorpamplona.amethyst.desktop.ui.chats.composer.EmojiPickerPanel
+import com.vitorpamplona.amethyst.desktop.ui.chats.composer.EmojiSuggestion
+import com.vitorpamplona.amethyst.desktop.ui.chats.composer.EmojiSuggestionStrip
+import com.vitorpamplona.amethyst.desktop.ui.chats.composer.GifPickerPanel
+import com.vitorpamplona.amethyst.desktop.ui.chats.composer.MentionSuggestions
+import com.vitorpamplona.amethyst.desktop.ui.chats.composer.standardEmojis
 import com.vitorpamplona.amethyst.desktop.ui.components.ToggleableTimeAgoText
 import com.vitorpamplona.amethyst.desktop.ui.media.DesktopFilePicker
 import com.vitorpamplona.amethyst.desktop.ui.media.MediaAttachmentRow
+import com.vitorpamplona.amethyst.desktop.ui.media.QualitySelectorChip
+import com.vitorpamplona.amethyst.desktop.ui.note.DesktopRichText
+import com.vitorpamplona.amethyst.desktop.ui.note.RichTextCallbacks
 import com.vitorpamplona.quartz.nip01Core.hints.EventHintBundle
 import com.vitorpamplona.quartz.nip04Dm.messages.PrivateDmEvent
 import com.vitorpamplona.quartz.nip17Dm.NIP17Factory
@@ -102,6 +134,7 @@ import com.vitorpamplona.quartz.nip17Dm.messages.ChatMessageEvent
 import com.vitorpamplona.quartz.nip17Dm.messages.changeSubject
 import com.vitorpamplona.quartz.nip94FileMetadata.tags.DimensionTag
 import com.vitorpamplona.quartz.utils.ciphers.AESGCM
+import kotlinx.coroutines.delay
 import kotlinx.coroutines.flow.StateFlow
 import kotlinx.coroutines.launch
 import java.awt.datatransfer.DataFlavor
@@ -114,6 +147,12 @@ private val isMacOS = System.getProperty("os.name").lowercase().contains("mac")
 private val MEDIA_EXTENSIONS =
     setOf("jpg", "jpeg", "png", "gif", "webp", "svg", "avif", "mp4", "webm", "mov", "mp3", "ogg", "wav", "flac")
 
+// Reencodable still-image types — gate the quality selector AND per-file
+// reencoding on these. GIF is excluded (animated GIFs pass through unchanged);
+// AVIF/HEIC are excluded because the reencoder rejects them (it would throw and
+// abort the send) — they upload as-is instead.
+private val IMAGE_EXTENSIONS = setOf("jpg", "jpeg", "png", "webp")
+
 /**
  * Right panel of the DM split-pane layout (flexible width).
  *
@@ -137,6 +176,8 @@ fun ChatPane(
     cacheProvider: ICacheProvider,
     feedViewModel: ChatroomFeedViewModel,
     messageState: ChatNewMessageState,
+    emojiPacks: EmojiPackState? = null,
+    attachedFiles: SnapshotStateList<File>,
     dmBroadcastStatus: DmBroadcastStatus = DmBroadcastStatus.Idle,
     onNavigateToProfile: (String) -> Unit = {},
     onBack: (() -> Unit)? = null,
@@ -148,12 +189,67 @@ fun ChatPane(
     val feedState by feedViewModel.feedState.feedContent.collectAsState()
     val messageText by messageState.message.collectAsState()
     val recipientsMissingRelays by messageState.recipientsMissingDmRelays.collectAsState()
+    val replyTo by messageState.replyTo.collectAsState()
 
-    // File attachment state
-    val attachedFiles = remember { mutableStateListOf<File>() }
+    // `:shortcode:` autocomplete: match the word under the caret against the
+    // account's selected NIP-30 packs AND standard unicode emoji shortcodes.
+    val myEmojis =
+        if (emojiPacks != null) {
+            emojiPacks.myEmojis.collectAsState().value
+        } else {
+            emptyList()
+        }
+    val currentWord = messageText.currentWord()
+    val emojiSuggestions =
+        remember(currentWord, myEmojis) {
+            if (currentWord.startsWith(":") && currentWord.length > 1) {
+                val code = currentWord.removePrefix(":")
+                val custom =
+                    myEmojis
+                        .filter { it.code.startsWith(code, ignoreCase = true) }
+                        .map { EmojiSuggestion(it.code, ":${it.code}:", previewUrl = it.link, previewGlyph = null) }
+                val standard =
+                    standardEmojis.mapNotNull { emoji ->
+                        val alias = emoji.details.aliases.firstOrNull { it.startsWith(code, ignoreCase = true) }
+                        alias?.let {
+                            EmojiSuggestion(it, emoji.details.string, previewUrl = null, previewGlyph = emoji.details.string)
+                        }
+                    }
+                (custom + standard).take(30)
+            } else {
+                emptyList()
+            }
+        }
+
+    // @mention autocomplete: search the cache for users matching the @word under
+    // the caret (done off the composition to avoid a cache scan every keystroke).
+    var mentionSuggestions by remember { mutableStateOf<List<User>>(emptyList()) }
+    LaunchedEffect(currentWord) {
+        mentionSuggestions =
+            if (currentWord.startsWith("@") && currentWord.length > 1) {
+                cacheProvider.findUsersStartingWith(currentWord.removePrefix("@"), 5)
+            } else {
+                emptyList()
+            }
+    }
+
+    // File attachment state is hoisted above the lock gate (see
+    // DeckColumnContainer) so it survives a lock/unlock cycle.
     var isUploading by remember { mutableStateOf(false) }
+    // True for the whole duration of a send (upload + publish) — drives the
+    // send-button spinner.
+    var isSending by remember { mutableStateOf(false) }
     val snackbarHostState = remember { SnackbarHostState() }
 
+    // Image compression: shared global default + optional per-composer override,
+    // reusing the same store the note composer uses. Override resets after send.
+    val defaultQuality by ImageCompressionStore.quality.collectAsState()
+    val stripExifSetting by ImageCompressionStore.stripExif.collectAsState()
+    val declareRealMimeType by ImageCompressionStore.encryptedMediaRealType.collectAsState()
+    var qualityOverride by remember { mutableStateOf<CompressionQuality?>(null) }
+    val activeQuality = qualityOverride ?: defaultQuality
+    val hasImageAttachment = attachedFiles.any { it.extension.lowercase() in IMAGE_EXTENSIONS }
+
     // Helper: attach files
     fun attachFiles(files: List<File>) {
         val mediaFiles = files.filter { it.extension.lowercase() in MEDIA_EXTENSIONS }
@@ -333,6 +429,7 @@ fun ChatPane(
                                     }
                                 }
                             },
+                            onReply = { messageState.setReply(it) },
                         )
                     }
 
@@ -362,44 +459,119 @@ fun ChatPane(
                     onPaste = {},
                     onRemove = { attachedFiles.remove(it) },
                 )
+                // Compression quality selector — only meaningful for reencodable images.
+                if (hasImageAttachment) {
+                    Row(modifier = Modifier.padding(horizontal = 8.dp, vertical = 2.dp)) {
+                        QualitySelectorChip(
+                            activeQuality = activeQuality,
+                            isOverride = qualityOverride != null,
+                            onSelect = { qualityOverride = it },
+                            onReset = { qualityOverride = null },
+                        )
+                    }
+                }
+            }
+
+            // @mention autocomplete dropdown
+            MentionSuggestions(
+                suggestions = mentionSuggestions,
+                onPick = { user ->
+                    onMentionPicked(messageState, messageText, user)
+                    mentionSuggestions = emptyList()
+                },
+            )
+
+            // `:shortcode:` autocomplete strip (custom packs + standard emoji)
+            EmojiSuggestionStrip(
+                suggestions = emojiSuggestions,
+                onPick = { suggestion ->
+                    messageState.updateMessage(messageText.replaceCurrentWord(suggestion.insertText))
+                },
+            )
+
+            // Reply-quote preview (NIP-17 threaded reply target)
+            replyTo?.let { replyNote ->
+                ReplyPreviewBar(
+                    note = replyNote,
+                    account = account,
+                    onDismiss = { messageState.clearReply() },
+                )
             }
 
             // Message input
             MessageInput(
-                messageText = messageText.text,
+                messageText = messageText,
                 recipientsMissingRelays = recipientsMissingRelays,
                 canSend = messageState.canSend || attachedFiles.isNotEmpty(),
                 isUploading = isUploading,
+                isSending = isSending,
                 hasAttachments = attachedFiles.isNotEmpty(),
-                onMessageChange = { messageState.updateMessage(messageText.copy(text = it)) },
+                onMessageChange = { messageState.updateMessage(it) },
                 onAttach = { attachFiles(DesktopFilePicker.pickMediaFiles()) },
                 onSend = {
                     scope.launch {
-                        if (attachedFiles.isNotEmpty()) {
-                            isUploading = true
-                            try {
-                                sendEncryptedFiles(
-                                    files = attachedFiles.toList(),
-                                    roomKey = roomKey,
-                                    account = account,
-                                    cacheProvider = cacheProvider,
-                                    blossomServers = blossomServers,
-                                )
-                                attachedFiles.clear()
-                            } catch (e: Exception) {
-                                // Keep files in attachment row for retry
-                                println("Encrypted file send failed: ${e.message}")
-                            } finally {
-                                isUploading = false
+                        isSending = true
+                        try {
+                            if (attachedFiles.isNotEmpty()) {
+                                isUploading = true
+                                try {
+                                    sendEncryptedFiles(
+                                        files = attachedFiles.toList(),
+                                        roomKey = roomKey,
+                                        account = account,
+                                        cacheProvider = cacheProvider,
+                                        blossomServers = blossomServers,
+                                        quality = activeQuality,
+                                        stripExif = stripExifSetting,
+                                        declareRealMimeType = declareRealMimeType,
+                                    )
+                                    attachedFiles.clear()
+                                    qualityOverride = null
+                                } catch (e: Exception) {
+                                    // Keep files in the attachment row for retry and
+                                    // surface the reason (console-only failures were
+                                    // invisible during testing).
+                                    println("Encrypted file send failed: ${e.message}")
+                                    val msg = e.message ?: e::class.simpleName.orEmpty()
+                                    val hint =
+                                        when {
+                                            // Server inspects the bytes and rejects the encrypted blob
+                                            // no matter what type we declare — it can't host private files.
+                                            "does not match" in msg || "expected application/json" in msg ->
+                                                " — this media server inspects uploads and can't host encrypted DM files. Switch to nostr.download in Media settings."
+                                            "415" in msg || "media type" in msg || "file type" in msg ->
+                                                " — this media server rejects private (opaque) uploads. Switch to one that accepts them (e.g. nostr.download), or enable “Reveal media type on encrypted DM uploads” in Media settings."
+                                            else -> ""
+                                        }
+                                    snackbarHostState.showSnackbar("Couldn't send attachment: $msg$hint")
+                                } finally {
+                                    isUploading = false
+                                }
                             }
-                        }
-                        // Also send text message if present
-                        if (messageState.canSend) {
-                            if (messageState.send()) {
+                            // Also send text message if present. Wrap in try/catch:
+                            // an uncaught throw here (e.g. a relay/signer error after
+                            // the message was already published) previously skipped
+                            // clear(), leaving the sent text/GIF stuck in the input.
+                            if (messageState.canSend) {
+                                try {
+                                    if (messageState.send()) {
+                                        messageState.clear()
+                                    }
+                                } catch (e: Exception) {
+                                    println("DM text send failed: ${e.message}")
+                                    // The message may already have been broadcast, so
+                                    // clear the composer and report the error rather
+                                    // than risk a duplicate on retry.
+                                    messageState.clear()
+                                    snackbarHostState.showSnackbar(
+                                        "Message sent, but a relay reported: ${e.message ?: e::class.simpleName}",
+                                    )
+                                }
+                            } else if (attachedFiles.isEmpty()) {
                                 messageState.clear()
                             }
-                        } else if (attachedFiles.isEmpty()) {
-                            messageState.clear()
+                        } finally {
+                            isSending = false
                         }
                     }
                 },
@@ -423,8 +595,13 @@ private fun MessageList(
     cacheProvider: ICacheProvider,
     onAuthorClick: (String) -> Unit,
     onReaction: (Note, String) -> Unit = { _, _ -> },
+    onReply: (Note) -> Unit = {},
 ) {
     val listState = rememberLazyListState()
+    val scope = rememberCoroutineScope()
+
+    // Message the user just jumped to via a reply preview — briefly highlighted.
+    var highlightedNoteId by remember { mutableStateOf<String?>(null) }
 
     // Auto-scroll to bottom when new messages arrive
     LaunchedEffect(messages.size) {
@@ -433,6 +610,19 @@ private fun MessageList(
         }
     }
 
+    // Scroll to the referenced message and flash it. No-op if it isn't loaded
+    // in the current window (older than what's on screen).
+    fun jumpToMessage(noteId: String) {
+        val index = messages.indexOfFirst { it.idHex == noteId }
+        if (index < 0) return
+        scope.launch {
+            listState.animateScrollToItem(index)
+            highlightedNoteId = noteId
+            delay(1600)
+            if (highlightedNoteId == noteId) highlightedNoteId = null
+        }
+    }
+
     LazyColumn(
         state = listState,
         reverseLayout = true,
@@ -448,8 +638,12 @@ private fun MessageList(
                 isMe = isMe,
                 isDraft = isDraft,
                 account = account,
+                cacheProvider = cacheProvider,
+                isHighlighted = note.idHex == highlightedNoteId,
                 onAuthorClick = onAuthorClick,
                 onReaction = { emoji -> onReaction(note, emoji) },
+                onReply = { onReply(note) },
+                onReplyContextClick = { parentId -> jumpToMessage(parentId) },
             )
         }
     }
@@ -477,13 +671,43 @@ private fun MessageWithReactions(
     isMe: Boolean,
     isDraft: Boolean,
     account: IAccount,
+    cacheProvider: ICacheProvider,
+    isHighlighted: Boolean = false,
     onAuthorClick: (String) -> Unit,
     onReaction: (String) -> Unit,
+    onReply: () -> Unit = {},
+    onReplyContextClick: (String) -> Unit = {},
 ) {
     var isHovered by remember { mutableStateOf(false) }
     var showPicker by remember { mutableStateOf(false) }
     val showIcon = (isHovered || showPicker) && !isDraft
 
+    // Reply-jump highlight: a brief bounce-in scale + background flash when the
+    // user taps a reply preview that points at this message.
+    val highlightScale by animateFloatAsState(
+        targetValue = if (isHighlighted) 1.03f else 1f,
+        animationSpec = spring(dampingRatio = Spring.DampingRatioMediumBouncy, stiffness = Spring.StiffnessLow),
+        label = "replyHighlightScale",
+    )
+    val highlightBg by animateColorAsState(
+        targetValue = if (isHighlighted) MaterialTheme.colorScheme.primary.copy(alpha = 0.12f) else Color.Transparent,
+        animationSpec = tween(durationMillis = 250),
+        label = "replyHighlightBg",
+    )
+
+    // The DM cache doesn't link Note.replyTo for chat messages, so resolve the
+    // replied-to parent from the event's reply e-tag directly.
+    val replyParent =
+        remember(note.idHex) {
+            val replyId =
+                when (val e = note.event) {
+                    is ChatMessageEvent -> e.replyTo().lastOrNull()
+                    is ChatMessageEncryptedFileHeaderEvent -> e.replyTo().lastOrNull()
+                    else -> null
+                }
+            replyId?.let { cacheProvider.getNoteIfExists(it) }
+        }
+
     // Decrypt NIP-04 content asynchronously; NIP-17 content is already plaintext
     val event = note.event
     var decryptedContent by remember(note.idHex) { mutableStateOf<String?>(null) }
@@ -515,7 +739,15 @@ private fun MessageWithReactions(
                 .onPointerEvent(PointerEventType.Enter) { isHovered = true }
                 .onPointerEvent(PointerEventType.Exit) { isHovered = false },
     ) {
-        Column {
+        Column(
+            modifier =
+                Modifier
+                    .graphicsLayer {
+                        scaleX = highlightScale
+                        scaleY = highlightScale
+                    }.clip(RoundedCornerShape(8.dp))
+                    .background(highlightBg),
+        ) {
             ChatMessageCompose(
                 note = note,
                 isLoggedInUser = isMe,
@@ -594,6 +826,23 @@ private fun MessageWithReactions(
                             }
                         }
 
+                        // Reply icon: same reserve-space + fade-on-hover treatment as
+                        // the reaction button. Sets the composer's reply target.
+                        Box(modifier = Modifier.alpha(if (showIcon) 1f else 0f)) {
+                            IconButton(
+                                onClick = onReply,
+                                enabled = showIcon,
+                                modifier = Modifier.size(20.dp),
+                            ) {
+                                Icon(
+                                    symbol = MaterialSymbols.Reply,
+                                    contentDescription = "Reply",
+                                    modifier = Modifier.size(14.dp),
+                                    tint = MaterialTheme.colorScheme.onSurfaceVariant,
+                                )
+                            }
+                        }
+
                         // AddReaction icon: always laid out to reserve space (so hover
                         // doesn't reflow the detail row and shift the whole list);
                         // alpha fades in/out based on hover.
@@ -630,18 +879,39 @@ private fun MessageWithReactions(
                     }
                 },
             ) { _ ->
-                when (note.event) {
-                    is ChatMessageEncryptedFileHeaderEvent -> {
-                        ChatFileAttachment(event = note.event as ChatMessageEncryptedFileHeaderEvent)
+                Column {
+                    // Replied-to message preview (tap to jump + highlight).
+                    replyParent?.let { parent ->
+                        MessageReplyContext(
+                            parent = parent,
+                            account = account,
+                            onClick = { onReplyContextClick(parent.idHex) },
+                        )
                     }
+                    when (note.event) {
+                        is ChatMessageEncryptedFileHeaderEvent -> {
+                            ChatFileAttachment(event = note.event as ChatMessageEncryptedFileHeaderEvent)
+                        }
 
-                    else -> {
-                        SelectionContainer {
-                            if (decryptedContent != null) {
-                                Text(
-                                    text = decryptedContent!!,
-                                    style = MaterialTheme.typography.bodyMedium,
-                                    color = MaterialTheme.colorScheme.onSurface,
+                        else -> {
+                            val content = decryptedContent
+                            if (content != null) {
+                                // Rich rendering so nostr:npub mentions resolve to
+                                // names, and image/GIF URLs (incl. picked GIFs) and
+                                // custom emoji render inline instead of as raw text.
+                                val tags =
+                                    remember(note.idHex) {
+                                        note.event?.tags?.toImmutableListOfLists() ?: EmptyTagList
+                                    }
+                                val richState =
+                                    remember(content, tags) {
+                                        CachedRichTextParser.parseText(content, tags)
+                                    }
+                                DesktopRichText(
+                                    content = content,
+                                    state = richState,
+                                    localCache = cacheProvider as? DesktopLocalCache,
+                                    callbacks = RichTextCallbacks(onMentionClick = onAuthorClick),
                                 )
                             } else {
                                 Text(
@@ -661,6 +931,71 @@ private fun MessageWithReactions(
     }
 }
 
+/**
+ * Small "replying to …" preview shown at the top of a reply message bubble.
+ * Shows the quoted author + a snippet; tapping it asks the list to jump to and
+ * highlight the original message. Mirrors the reply chips in Signal/WhatsApp/
+ * Telegram.
+ */
+@Composable
+private fun MessageReplyContext(
+    parent: Note,
+    account: IAccount,
+    onClick: () -> Unit,
+) {
+    var preview by remember(parent.idHex) { mutableStateOf("") }
+    LaunchedEffect(parent.idHex) {
+        preview =
+            when (val e = parent.event) {
+                is ChatMessageEncryptedFileHeaderEvent -> "📎 Attachment"
+                is PrivateDmEvent ->
+                    try {
+                        e.decryptContent(account.signer)
+                    } catch (_: Exception) {
+                        ""
+                    }
+
+                else -> e?.content ?: ""
+            }
+    }
+    Row(
+        verticalAlignment = Alignment.CenterVertically,
+        modifier =
+            Modifier
+                .padding(bottom = 4.dp)
+                .clip(RoundedCornerShape(6.dp))
+                .clickable(onClick = onClick)
+                .background(MaterialTheme.colorScheme.surfaceVariant.copy(alpha = 0.5f))
+                .padding(horizontal = 8.dp, vertical = 4.dp),
+    ) {
+        Box(
+            modifier =
+                Modifier
+                    .width(3.dp)
+                    .height(28.dp)
+                    .clip(RoundedCornerShape(2.dp))
+                    .background(MaterialTheme.colorScheme.primary),
+        )
+        Spacer(Modifier.width(6.dp))
+        Column {
+            Text(
+                text = parent.author?.toBestDisplayName() ?: "Unknown",
+                style = MaterialTheme.typography.labelSmall,
+                color = MaterialTheme.colorScheme.primary,
+                maxLines = 1,
+                overflow = TextOverflow.Ellipsis,
+            )
+            Text(
+                text = preview,
+                style = MaterialTheme.typography.bodySmall,
+                color = MaterialTheme.colorScheme.onSurfaceVariant,
+                maxLines = 1,
+                overflow = TextOverflow.Ellipsis,
+            )
+        }
+    }
+}
+
 /**
  * Sends a NIP-17 gift-wrapped reaction to a note within a group DM.
  */
@@ -724,20 +1059,98 @@ private fun ReactionBar(onReaction: (String) -> Unit) {
     }
 }
 
+/**
+ * Preview bar shown above the composer when a message is selected as the reply
+ * target. Mirrors Android's DisplayReplyingToNote: quoted author + snippet +
+ * dismiss. On send, [ChatNewMessageState] threads the reply via
+ * ChatMessageEvent.reply().
+ */
+@Composable
+private fun ReplyPreviewBar(
+    note: Note,
+    account: IAccount,
+    onDismiss: () -> Unit,
+) {
+    val event = note.event
+    var preview by remember(note.idHex) { mutableStateOf("") }
+    LaunchedEffect(note.idHex, event) {
+        preview =
+            when (event) {
+                is ChatMessageEncryptedFileHeaderEvent -> "📎 Attachment"
+                is PrivateDmEvent ->
+                    try {
+                        event.decryptContent(account.signer)
+                    } catch (_: Exception) {
+                        ""
+                    }
+
+                else -> event?.content ?: ""
+            }
+    }
+
+    Surface(
+        color = MaterialTheme.colorScheme.surfaceVariant.copy(alpha = 0.5f),
+        modifier = Modifier.fillMaxWidth(),
+    ) {
+        Row(
+            verticalAlignment = Alignment.CenterVertically,
+            modifier = Modifier.fillMaxWidth().padding(horizontal = 12.dp, vertical = 6.dp),
+        ) {
+            Icon(
+                symbol = MaterialSymbols.Reply,
+                contentDescription = null,
+                modifier = Modifier.size(16.dp),
+                tint = MaterialTheme.colorScheme.primary,
+            )
+            Spacer(Modifier.width(8.dp))
+            Column(modifier = Modifier.weight(1f)) {
+                Text(
+                    text = note.author?.toBestDisplayName() ?: "Unknown",
+                    style = MaterialTheme.typography.labelSmall,
+                    color = MaterialTheme.colorScheme.primary,
+                    maxLines = 1,
+                    overflow = TextOverflow.Ellipsis,
+                )
+                Text(
+                    text = preview,
+                    style = MaterialTheme.typography.bodySmall,
+                    color = MaterialTheme.colorScheme.onSurfaceVariant,
+                    maxLines = 1,
+                    overflow = TextOverflow.Ellipsis,
+                )
+            }
+            IconButton(
+                onClick = onDismiss,
+                modifier = Modifier.size(28.dp),
+            ) {
+                Icon(
+                    symbol = MaterialSymbols.Close,
+                    contentDescription = "Cancel reply",
+                    modifier = Modifier.size(16.dp),
+                    tint = MaterialTheme.colorScheme.onSurfaceVariant,
+                )
+            }
+        }
+    }
+}
+
 /**
  * Message input area at the bottom of the chat pane.
  */
 @Composable
 private fun MessageInput(
-    messageText: String,
+    messageText: TextFieldValue,
     recipientsMissingRelays: Boolean,
     canSend: Boolean,
     isUploading: Boolean = false,
+    isSending: Boolean = false,
     hasAttachments: Boolean = false,
-    onMessageChange: (String) -> Unit,
+    onMessageChange: (TextFieldValue) -> Unit,
     onAttach: () -> Unit = {},
     onSend: () -> Unit,
 ) {
+    var showEmojiPicker by remember { mutableStateOf(false) }
+    var showGifPicker by remember { mutableStateOf(false) }
     Column(modifier = Modifier.fillMaxWidth().padding(8.dp)) {
         Row(
             modifier = Modifier.fillMaxWidth(),
@@ -799,7 +1212,7 @@ private fun MessageInput(
                 interactionSource = messageInteraction,
                 decorationBox = { innerTextField ->
                     androidx.compose.material3.OutlinedTextFieldDefaults.DecorationBox(
-                        value = messageText,
+                        value = messageText.text,
                         innerTextField = innerTextField,
                         enabled = true,
                         singleLine = false,
@@ -828,21 +1241,91 @@ private fun MessageInput(
                 },
             )
 
+            // Emoji picker
+            Box {
+                IconButton(
+                    onClick = { showEmojiPicker = !showEmojiPicker },
+                    enabled = !isUploading,
+                    modifier = Modifier.size(40.dp),
+                ) {
+                    Icon(
+                        symbol = MaterialSymbols.EmojiEmotions,
+                        contentDescription = "Emoji",
+                        tint = MaterialTheme.colorScheme.primary,
+                    )
+                }
+                if (showEmojiPicker) {
+                    Popup(
+                        alignment = Alignment.BottomEnd,
+                        offset = IntOffset(0, -48),
+                        onDismissRequest = { showEmojiPicker = false },
+                        properties = PopupProperties(focusable = true),
+                    ) {
+                        EmojiPickerPanel(
+                            onPick = { emoji ->
+                                onMessageChange(insertAtCursor(messageText, emoji))
+                            },
+                        )
+                    }
+                }
+            }
+
+            // GIF picker (Nostr-native, NIP-94)
+            Box {
+                TextButton(
+                    onClick = { showGifPicker = !showGifPicker },
+                    enabled = !isUploading,
+                    modifier = Modifier.size(width = 44.dp, height = 40.dp),
+                    contentPadding =
+                        androidx.compose.foundation.layout
+                            .PaddingValues(0.dp),
+                ) {
+                    Text(
+                        text = "GIF",
+                        style = MaterialTheme.typography.labelMedium,
+                        color = MaterialTheme.colorScheme.primary,
+                    )
+                }
+                if (showGifPicker) {
+                    Popup(
+                        alignment = Alignment.BottomEnd,
+                        offset = IntOffset(0, -48),
+                        onDismissRequest = { showGifPicker = false },
+                        properties = PopupProperties(focusable = true),
+                    ) {
+                        GifPickerPanel(
+                            onPick = { url ->
+                                onMessageChange(messageText.insertUrlAtCursor(url))
+                                showGifPicker = false
+                            },
+                        )
+                    }
+                }
+            }
+
             IconButton(
                 onClick = onSend,
-                enabled = canSend && !isUploading,
+                enabled = canSend && !isSending,
                 modifier = Modifier.size(40.dp),
             ) {
-                Icon(
-                    MaterialSymbols.AutoMirrored.Send,
-                    contentDescription = "Send",
-                    tint =
-                        if (canSend && !isUploading) {
-                            MaterialTheme.colorScheme.primary
-                        } else {
-                            MaterialTheme.colorScheme.onSurfaceVariant.copy(alpha = 0.3f)
-                        },
-                )
+                if (isSending) {
+                    CircularProgressIndicator(
+                        modifier = Modifier.size(20.dp),
+                        strokeWidth = 2.dp,
+                        color = MaterialTheme.colorScheme.primary,
+                    )
+                } else {
+                    Icon(
+                        MaterialSymbols.AutoMirrored.Send,
+                        contentDescription = "Send",
+                        tint =
+                            if (canSend) {
+                                MaterialTheme.colorScheme.primary
+                            } else {
+                                MaterialTheme.colorScheme.onSurfaceVariant.copy(alpha = 0.3f)
+                            },
+                    )
+                }
             }
         }
 
@@ -876,6 +1359,33 @@ private fun MessageInput(
     }
 }
 
+/**
+ * Insert [insert] at the caret (replacing any selection) and place the caret
+ * immediately after it. Shared by the emoji picker, custom-emoji / mention
+ * autocomplete, and GIF picker to write into the composer's TextFieldValue.
+ */
+internal fun insertAtCursor(
+    current: TextFieldValue,
+    insert: String,
+): TextFieldValue {
+    val sel = current.selection
+    val newText = current.text.replaceRange(sel.min, sel.max, insert)
+    val cursor = sel.min + insert.length
+    return TextFieldValue(text = newText, selection = TextRange(cursor))
+}
+
+/**
+ * Replaces the `@word` under the caret with a `nostr:npub…` reference (plus a
+ * trailing space), mirroring the note composer's mention insertion.
+ */
+private fun onMentionPicked(
+    messageState: ChatNewMessageState,
+    current: TextFieldValue,
+    user: User,
+) {
+    messageState.updateMessage(current.replaceCurrentWord("nostr:${user.pubkeyNpub()} "))
+}
+
 /**
  * Encrypts and uploads files, then sends each as a ChatMessageEncryptedFileHeaderEvent (kind 15)
  * wrapped in GiftWrap for each recipient.
@@ -886,6 +1396,9 @@ private suspend fun sendEncryptedFiles(
     account: IAccount,
     cacheProvider: ICacheProvider,
     blossomServers: StateFlow<List<String>>?,
+    quality: CompressionQuality? = null,
+    stripExif: Boolean = true,
+    declareRealMimeType: Boolean = false,
 ) {
     val orchestrator = UploadOrchestrator()
     val server = blossomServers?.value?.firstOrNull() ?: DEFAULT_BLOSSOM_SERVER
@@ -893,7 +1406,12 @@ private suspend fun sendEncryptedFiles(
 
     for (file in files) {
         val cipher = AESGCM()
-        val result = orchestrator.uploadEncrypted(file, cipher, server, account.signer)
+        // Only re-encode genuinely reencodable raster images; everything else
+        // (video, audio, GIF, AVIF/HEIC, unknown) uploads unchanged so a single
+        // unsupported file can't abort the whole send.
+        val fileQuality = if (file.extension.lowercase() in IMAGE_EXTENSIONS) quality else null
+        val result =
+            orchestrator.uploadEncrypted(file, cipher, server, account.signer, stripExif, fileQuality, declareRealMimeType)
         val url = result.blossom.url ?: continue
 
         val template =

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/DesktopMessagesScreen.kt

@@ -44,6 +44,7 @@ import androidx.compose.runtime.mutableStateOf
 import androidx.compose.runtime.remember
 import androidx.compose.runtime.rememberCoroutineScope
 import androidx.compose.runtime.setValue
+import androidx.compose.runtime.snapshots.SnapshotStateList
 import androidx.compose.ui.Alignment
 import androidx.compose.ui.Modifier
 import androidx.compose.ui.focus.FocusRequester
@@ -63,6 +64,7 @@ import com.vitorpamplona.amethyst.commons.icons.symbols.Icon
 import com.vitorpamplona.amethyst.commons.icons.symbols.MaterialSymbols
 import com.vitorpamplona.amethyst.commons.model.IAccount
 import com.vitorpamplona.amethyst.commons.model.cache.ICacheProvider
+import com.vitorpamplona.amethyst.commons.model.nip30CustomEmojis.EmojiPackState
 import com.vitorpamplona.amethyst.commons.viewmodels.ChatNewMessageState
 import com.vitorpamplona.amethyst.commons.viewmodels.ChatroomFeedViewModel
 import com.vitorpamplona.amethyst.desktop.cache.DesktopLocalCache
@@ -73,6 +75,7 @@ import com.vitorpamplona.quartz.nip17Dm.base.ChatroomKey
 import kotlinx.coroutines.CoroutineScope
 import kotlinx.coroutines.launch
 import java.awt.Cursor
+import java.io.File
 
 private val isMacOS = System.getProperty("os.name").lowercase().contains("mac")
 
@@ -93,14 +96,17 @@ fun DesktopMessagesScreen(
     localCache: DesktopLocalCache,
     compactMode: Boolean = false,
     onNavigateToProfile: (String) -> Unit = {},
+    // Hoisted above the lock gate (see DeckColumnContainer) so a lock/unlock
+    // cycle preserves the selected conversation + draft + attachments.
+    // messageState is null only when no room is selected.
+    listState: ChatroomListState,
+    emojiPacks: EmojiPackState,
+    messageState: ChatNewMessageState?,
+    attachedFiles: SnapshotStateList<File>,
 ) {
     val scope = rememberCoroutineScope()
     val accountRelays = com.vitorpamplona.amethyst.desktop.ui.relay.LocalAccountRelays.current
     var showDmRelayPicker by remember { mutableStateOf(false) }
-    val listState =
-        remember(account) {
-            ChatroomListState(account, cacheProvider, relayManager, localCache, scope)
-        }
     val selectedRoom by listState.selectedRoom.collectAsState()
     val listFocusRequester = remember { FocusRequester() }
     var showNewDmDialog by remember { mutableStateOf(false) }
@@ -158,6 +164,9 @@ fun DesktopMessagesScreen(
                         account = account,
                         cacheProvider = cacheProvider,
                         scope = scope,
+                        emojiPacks = emojiPacks,
+                        messageState = messageState,
+                        attachedFiles = attachedFiles,
                         onNavigateToProfile = onNavigateToProfile,
                         listFocusRequester = listFocusRequester,
                         onShowNewDm = { showNewDmDialog = true },
@@ -171,6 +180,9 @@ fun DesktopMessagesScreen(
                         account = account,
                         cacheProvider = cacheProvider,
                         scope = scope,
+                        emojiPacks = emojiPacks,
+                        messageState = messageState,
+                        attachedFiles = attachedFiles,
                         onNavigateToProfile = onNavigateToProfile,
                         listFocusRequester = listFocusRequester,
                         onShowNewDm = { showNewDmDialog = true },
@@ -242,6 +254,9 @@ private fun CompactMessagesContent(
     account: IAccount,
     cacheProvider: ICacheProvider,
     scope: CoroutineScope,
+    emojiPacks: EmojiPackState,
+    messageState: ChatNewMessageState?,
+    attachedFiles: SnapshotStateList<File>,
     onNavigateToProfile: (String) -> Unit,
     listFocusRequester: FocusRequester,
     onShowNewDm: () -> Unit,
@@ -250,23 +265,11 @@ private fun CompactMessagesContent(
 ) {
     Box(modifier = Modifier.fillMaxSize().then(keyHandler)) {
         val currentRoom = selectedRoom
-        if (currentRoom != null) {
+        if (currentRoom != null && messageState != null) {
             val feedViewModel =
                 remember(currentRoom) {
                     ChatroomFeedViewModel(currentRoom, account, cacheProvider)
                 }
-            val messageState =
-                remember(currentRoom) {
-                    ChatNewMessageState(
-                        account,
-                        cacheProvider,
-                        scope,
-                        dmInboxResolver =
-                            (account as? DesktopIAccount)?.dmInboxResolver?.let { resolver ->
-                                { hexKey -> resolver.resolve(hexKey) }
-                            },
-                    )
-                }
             val broadcastStatus =
                 if (account is DesktopIAccount) {
                     account.dmSendTracker.status
@@ -282,6 +285,8 @@ private fun CompactMessagesContent(
                 cacheProvider = cacheProvider,
                 feedViewModel = feedViewModel,
                 messageState = messageState,
+                emojiPacks = emojiPacks,
+                attachedFiles = attachedFiles,
                 dmBroadcastStatus = broadcastStatus,
                 onNavigateToProfile = onNavigateToProfile,
                 onBack = { listState.clearSelection() },
@@ -311,6 +316,9 @@ private fun SplitMessagesContent(
     account: IAccount,
     cacheProvider: ICacheProvider,
     scope: CoroutineScope,
+    emojiPacks: EmojiPackState,
+    messageState: ChatNewMessageState?,
+    attachedFiles: SnapshotStateList<File>,
     onNavigateToProfile: (String) -> Unit,
     listFocusRequester: FocusRequester,
     onShowNewDm: () -> Unit,
@@ -354,23 +362,11 @@ private fun SplitMessagesContent(
                     .background(MaterialTheme.colorScheme.surface),
         ) {
             val currentRoom = selectedRoom
-            if (currentRoom != null) {
+            if (currentRoom != null && messageState != null) {
                 val feedViewModel =
                     remember(currentRoom) {
                         ChatroomFeedViewModel(currentRoom, account, cacheProvider)
                     }
-                val messageState =
-                    remember(currentRoom) {
-                        ChatNewMessageState(
-                            account,
-                            cacheProvider,
-                            scope,
-                            dmInboxResolver =
-                                (account as? DesktopIAccount)?.dmInboxResolver?.let { resolver ->
-                                    { hexKey -> resolver.resolve(hexKey) }
-                                },
-                        )
-                    }
                 val broadcastStatus =
                     if (account is DesktopIAccount) {
                         account.dmSendTracker.status
@@ -386,6 +382,8 @@ private fun SplitMessagesContent(
                     cacheProvider = cacheProvider,
                     feedViewModel = feedViewModel,
                     messageState = messageState,
+                    emojiPacks = emojiPacks,
+                    attachedFiles = attachedFiles,
                     dmBroadcastStatus = broadcastStatus,
                     onNavigateToProfile = onNavigateToProfile,
                 )

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/composer/EmojiPickerPanel.kt

@@ -0,0 +1,129 @@
+/*
+ * Copyright (c) 2025 Vitor Pamplona
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to use,
+ * copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the
+ * Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN
+ * AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
+ * WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+package com.vitorpamplona.amethyst.desktop.ui.chats.composer
+
+import androidx.compose.foundation.clickable
+import androidx.compose.foundation.layout.Box
+import androidx.compose.foundation.layout.Column
+import androidx.compose.foundation.layout.fillMaxWidth
+import androidx.compose.foundation.layout.heightIn
+import androidx.compose.foundation.layout.padding
+import androidx.compose.foundation.layout.size
+import androidx.compose.foundation.lazy.grid.GridCells
+import androidx.compose.foundation.lazy.grid.LazyVerticalGrid
+import androidx.compose.foundation.lazy.grid.items
+import androidx.compose.foundation.shape.RoundedCornerShape
+import androidx.compose.material3.MaterialTheme
+import androidx.compose.material3.OutlinedTextField
+import androidx.compose.material3.Surface
+import androidx.compose.material3.Text
+import androidx.compose.runtime.Composable
+import androidx.compose.runtime.getValue
+import androidx.compose.runtime.mutableStateOf
+import androidx.compose.runtime.remember
+import androidx.compose.runtime.setValue
+import androidx.compose.ui.Alignment
+import androidx.compose.ui.Modifier
+import androidx.compose.ui.input.pointer.PointerIcon
+import androidx.compose.ui.input.pointer.pointerHoverIcon
+import androidx.compose.ui.text.style.TextAlign
+import androidx.compose.ui.unit.dp
+import androidx.compose.ui.unit.sp
+
+/**
+ * A compact unicode emoji picker for the desktop DM composer. Renders emojis as
+ * text via the platform's system emoji font (offline, no network) using the
+ * Kodein Emoji.kt data API. [onPick] receives the UTF-16 emoji string to insert
+ * at the caret.
+ */
+@Composable
+fun EmojiPickerPanel(
+    onPick: (String) -> Unit,
+    modifier: Modifier = Modifier,
+) {
+    var query by remember { mutableStateOf("") }
+
+    // Shared flat list of all emojis (built once, static emoji-kt data — no
+    // network/service init needed).
+    val filtered =
+        remember(query) {
+            if (query.isBlank()) {
+                standardEmojis
+            } else {
+                val q = query.trim().lowercase()
+                standardEmojis.filter {
+                    it.details.description
+                        .lowercase()
+                        .contains(q)
+                }
+            }
+        }
+
+    Surface(
+        shape = RoundedCornerShape(12.dp),
+        color = MaterialTheme.colorScheme.surface,
+        shadowElevation = 4.dp,
+        tonalElevation = 2.dp,
+        modifier = modifier.size(width = 320.dp, height = 360.dp),
+    ) {
+        Column(modifier = Modifier.padding(8.dp)) {
+            OutlinedTextField(
+                value = query,
+                onValueChange = { query = it },
+                singleLine = true,
+                placeholder = { Text("Search emoji…") },
+                textStyle = MaterialTheme.typography.bodyMedium,
+                modifier = Modifier.fillMaxWidth(),
+            )
+
+            if (filtered.isEmpty()) {
+                Box(
+                    modifier = Modifier.fillMaxWidth().heightIn(min = 60.dp),
+                    contentAlignment = Alignment.Center,
+                ) {
+                    Text(
+                        "No emoji found",
+                        style = MaterialTheme.typography.bodySmall,
+                        color = MaterialTheme.colorScheme.onSurfaceVariant,
+                    )
+                }
+            } else {
+                LazyVerticalGrid(
+                    columns = GridCells.Adaptive(minSize = 36.dp),
+                    modifier = Modifier.fillMaxWidth().padding(top = 4.dp),
+                ) {
+                    items(filtered, key = { it.details.description }) { emoji ->
+                        Text(
+                            text = emoji.details.string,
+                            fontSize = 22.sp,
+                            textAlign = TextAlign.Center,
+                            modifier =
+                                Modifier
+                                    .size(36.dp)
+                                    .pointerHoverIcon(PointerIcon.Hand)
+                                    .clickable { onPick(emoji.details.string) },
+                        )
+                    }
+                }
+            }
+        }
+    }
+}

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/composer/EmojiSuggestion.kt

@@ -0,0 +1,120 @@
+/*
+ * Copyright (c) 2025 Vitor Pamplona
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to use,
+ * copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the
+ * Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN
+ * AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
+ * WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+package com.vitorpamplona.amethyst.desktop.ui.chats.composer
+
+import androidx.compose.foundation.clickable
+import androidx.compose.foundation.layout.Row
+import androidx.compose.foundation.layout.fillMaxWidth
+import androidx.compose.foundation.layout.heightIn
+import androidx.compose.foundation.layout.padding
+import androidx.compose.foundation.layout.size
+import androidx.compose.foundation.lazy.LazyRow
+import androidx.compose.foundation.lazy.items
+import androidx.compose.material3.MaterialTheme
+import androidx.compose.material3.Surface
+import androidx.compose.material3.Text
+import androidx.compose.runtime.Composable
+import androidx.compose.ui.Alignment
+import androidx.compose.ui.Modifier
+import androidx.compose.ui.input.pointer.PointerIcon
+import androidx.compose.ui.input.pointer.pointerHoverIcon
+import androidx.compose.ui.unit.dp
+import androidx.compose.ui.unit.sp
+import coil3.compose.AsyncImage
+import org.kodein.emoji.Emoji
+import org.kodein.emoji.allGroups
+import org.kodein.emoji.allOf
+
+/**
+ * One `:shortcode:` autocomplete entry — either a NIP-30 custom-pack emoji
+ * (rendered from [previewUrl], inserts `:code:`) or a standard unicode emoji
+ * (rendered as [previewGlyph], inserts the glyph itself).
+ */
+data class EmojiSuggestion(
+    val label: String,
+    val insertText: String,
+    val previewUrl: String?,
+    val previewGlyph: String?,
+)
+
+/**
+ * The full flat list of standard unicode emojis, built once from the Kodein
+ * emoji-kt static data (no network/service init needed). Shared by the emoji
+ * picker and the `:` shortcode autocomplete.
+ */
+internal val standardEmojis: List<Emoji> by lazy {
+    Emoji.allGroups().flatMap { group -> Emoji.allOf(group) }
+}
+
+/**
+ * Horizontal `:shortcode:` autocomplete strip shown above the composer while the
+ * word under the caret starts with `:`. Renders custom-pack emojis (image) and
+ * standard emojis (glyph) side by side. [onPick] returns the chosen entry so the
+ * caller can replace the current word with its [EmojiSuggestion.insertText].
+ */
+@Composable
+fun EmojiSuggestionStrip(
+    suggestions: List<EmojiSuggestion>,
+    onPick: (EmojiSuggestion) -> Unit,
+    modifier: Modifier = Modifier,
+) {
+    if (suggestions.isEmpty()) return
+
+    Surface(
+        color = MaterialTheme.colorScheme.surfaceVariant.copy(alpha = 0.6f),
+        modifier = modifier.fillMaxWidth(),
+    ) {
+        LazyRow(
+            modifier = Modifier.fillMaxWidth().heightIn(min = 44.dp).padding(horizontal = 8.dp, vertical = 4.dp),
+        ) {
+            items(suggestions, key = { "${it.label}|${it.insertText}" }) { suggestion ->
+                Row(
+                    verticalAlignment = Alignment.CenterVertically,
+                    modifier =
+                        Modifier
+                            .padding(horizontal = 4.dp)
+                            .pointerHoverIcon(PointerIcon.Hand)
+                            .clickable { onPick(suggestion) },
+                ) {
+                    if (suggestion.previewUrl != null) {
+                        AsyncImage(
+                            model = suggestion.previewUrl,
+                            contentDescription = suggestion.label,
+                            modifier = Modifier.size(28.dp).padding(end = 4.dp),
+                        )
+                    } else if (suggestion.previewGlyph != null) {
+                        Text(
+                            text = suggestion.previewGlyph,
+                            fontSize = 20.sp,
+                            modifier = Modifier.padding(end = 4.dp),
+                        )
+                    }
+                    Text(
+                        text = ":${suggestion.label}:",
+                        style = MaterialTheme.typography.bodySmall,
+                        color = MaterialTheme.colorScheme.onSurface,
+                        modifier = Modifier.padding(end = 4.dp),
+                    )
+                }
+            }
+        }
+    }
+}

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/composer/GifPickerPanel.kt

@@ -0,0 +1,147 @@
+/*
+ * Copyright (c) 2025 Vitor Pamplona
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to use,
+ * copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the
+ * Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN
+ * AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
+ * WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+package com.vitorpamplona.amethyst.desktop.ui.chats.composer
+
+import androidx.compose.foundation.clickable
+import androidx.compose.foundation.layout.Box
+import androidx.compose.foundation.layout.Column
+import androidx.compose.foundation.layout.aspectRatio
+import androidx.compose.foundation.layout.fillMaxSize
+import androidx.compose.foundation.layout.fillMaxWidth
+import androidx.compose.foundation.layout.padding
+import androidx.compose.foundation.layout.size
+import androidx.compose.foundation.lazy.grid.GridCells
+import androidx.compose.foundation.lazy.grid.LazyVerticalGrid
+import androidx.compose.foundation.lazy.grid.items
+import androidx.compose.foundation.shape.RoundedCornerShape
+import androidx.compose.material3.CircularProgressIndicator
+import androidx.compose.material3.MaterialTheme
+import androidx.compose.material3.OutlinedTextField
+import androidx.compose.material3.Surface
+import androidx.compose.material3.Text
+import androidx.compose.runtime.Composable
+import androidx.compose.runtime.LaunchedEffect
+import androidx.compose.runtime.getValue
+import androidx.compose.runtime.mutableStateOf
+import androidx.compose.runtime.remember
+import androidx.compose.runtime.setValue
+import androidx.compose.ui.Alignment
+import androidx.compose.ui.Modifier
+import androidx.compose.ui.input.pointer.PointerIcon
+import androidx.compose.ui.input.pointer.pointerHoverIcon
+import androidx.compose.ui.unit.dp
+import coil3.compose.AsyncImage
+import com.vitorpamplona.amethyst.desktop.DesktopPreferences
+import com.vitorpamplona.amethyst.desktop.ui.deck.LocalRelayManager
+import com.vitorpamplona.amethyst.desktop.ui.media.AnimatedGifImage
+import com.vitorpamplona.amethyst.desktop.ui.media.isAnimatedGifUrl
+import kotlinx.coroutines.delay
+
+/**
+ * Nostr-native GIF search picker for the DM composer. Queries the configured
+ * NIP-94 GIF relays (default GIF Buddy) via the app's own relay client and
+ * inserts the chosen GIF's hosted URL into the message. No third-party GIF API.
+ */
+@Composable
+fun GifPickerPanel(
+    onPick: (String) -> Unit,
+    modifier: Modifier = Modifier,
+) {
+    val relayManager = LocalRelayManager.current
+    var query by remember { mutableStateOf("") }
+    var results by remember { mutableStateOf<List<GifResult>>(emptyList()) }
+    var loading by remember { mutableStateOf(false) }
+
+    // Debounced search: re-run ~350ms after the query settles. A blank query
+    // loads the newest GIFs from the relays.
+    LaunchedEffect(query, relayManager) {
+        val client = relayManager?.client
+        if (client == null) {
+            results = emptyList()
+            return@LaunchedEffect
+        }
+        loading = true
+        delay(350)
+        results = searchGifs(client, DesktopPreferences.gifRelays, query)
+        loading = false
+    }
+
+    Surface(
+        shape = RoundedCornerShape(12.dp),
+        color = MaterialTheme.colorScheme.surface,
+        shadowElevation = 4.dp,
+        tonalElevation = 2.dp,
+        modifier = modifier.size(width = 340.dp, height = 380.dp),
+    ) {
+        Column(modifier = Modifier.padding(8.dp)) {
+            OutlinedTextField(
+                value = query,
+                onValueChange = { query = it },
+                singleLine = true,
+                placeholder = { Text("Search GIFs…") },
+                textStyle = MaterialTheme.typography.bodyMedium,
+                modifier = Modifier.fillMaxWidth(),
+            )
+
+            Box(modifier = Modifier.fillMaxSize().padding(top = 4.dp), contentAlignment = Alignment.Center) {
+                when {
+                    loading -> CircularProgressIndicator(modifier = Modifier.size(28.dp))
+                    results.isEmpty() ->
+                        Text(
+                            "No GIFs found",
+                            style = MaterialTheme.typography.bodySmall,
+                            color = MaterialTheme.colorScheme.onSurfaceVariant,
+                        )
+                    else ->
+                        LazyVerticalGrid(
+                            columns = GridCells.Adaptive(minSize = 96.dp),
+                            modifier = Modifier.fillMaxSize(),
+                        ) {
+                            items(results, key = { it.url }) { gif ->
+                                val cellModifier =
+                                    Modifier
+                                        .padding(2.dp)
+                                        .fillMaxWidth()
+                                        .aspectRatio(1f)
+                                        .pointerHoverIcon(PointerIcon.Hand)
+                                        .clickable { onPick(gif.url) }
+                                // Animate GIFs (the whole grid is GIFs); fall back
+                                // to a static frame for any non-.gif URL.
+                                if (isAnimatedGifUrl(gif.url)) {
+                                    AnimatedGifImage(
+                                        url = gif.url,
+                                        contentDescription = gif.description,
+                                        modifier = cellModifier,
+                                    )
+                                } else {
+                                    AsyncImage(
+                                        model = gif.url,
+                                        contentDescription = gif.description,
+                                        modifier = cellModifier,
+                                    )
+                                }
+                            }
+                        }
+                }
+            }
+        }
+    }
+}

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/composer/GifResult.kt

@@ -0,0 +1,94 @@
+/*
+ * Copyright (c) 2025 Vitor Pamplona
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to use,
+ * copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the
+ * Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN
+ * AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
+ * WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+package com.vitorpamplona.amethyst.desktop.ui.chats.composer
+
+import com.vitorpamplona.quartz.nip01Core.relay.client.INostrClient
+import com.vitorpamplona.quartz.nip01Core.relay.client.accessories.fetchAll
+import com.vitorpamplona.quartz.nip01Core.relay.filters.Filter
+import com.vitorpamplona.quartz.nip94FileMetadata.FileHeaderEvent
+
+/** A single GIF result surfaced from a NIP-94 (kind 1063) metadata event. */
+data class GifResult(
+    val url: String,
+    val description: String,
+)
+
+/**
+ * Nostr-native GIF search. Queries the given [relays] for NIP-94 kind-1063
+ * file-metadata events tagged `m=image/gif` (the shape GIF Buddy publishes),
+ * merges + dedups by URL across relays, and filters client-side by [query]
+ * (the default relay has no NIP-50, so matching is done here). No third-party
+ * GIF API, no API key — just relay REQs on the app's own (Tor-aware) client.
+ */
+suspend fun searchGifs(
+    client: INostrClient,
+    relays: List<String>,
+    query: String,
+    limitPerRelay: Int = 100,
+): List<GifResult> {
+    val trimmed = query.trim()
+    val filter =
+        Filter(
+            kinds = listOf(FileHeaderEvent.KIND),
+            tags = mapOf("m" to listOf("image/gif")),
+            limit = limitPerRelay,
+            search = trimmed.ifBlank { null },
+        )
+
+    val raw = mutableListOf<GifResult>()
+    for (relay in relays) {
+        val events =
+            runCatching { client.fetchAll(relay, filter, idleTimeoutMs = 8_000L) }
+                .getOrDefault(emptyList())
+        for (event in events) {
+            val fileHeader = event as? FileHeaderEvent ?: continue
+            val url = fileHeader.url() ?: continue
+            raw.add(GifResult(url = url, description = fileHeader.content))
+        }
+    }
+    return mergeGifResults(raw, trimmed)
+}
+
+/**
+ * Dedups [raw] GIF results by URL (keeping first-seen order — newest-first since
+ * fetchAll sorts descending) and, when [query] is non-blank, filters to entries
+ * whose description or URL contains it (case-insensitive). Pure so it can be
+ * unit-tested without a relay client.
+ */
+internal fun mergeGifResults(
+    raw: List<GifResult>,
+    query: String,
+): List<GifResult> {
+    val byUrl = LinkedHashMap<String, GifResult>()
+    for (gif in raw) {
+        if (!byUrl.containsKey(gif.url)) byUrl[gif.url] = gif
+    }
+    val all = byUrl.values.toList()
+    val trimmed = query.trim()
+    return if (trimmed.isBlank()) {
+        all
+    } else {
+        all.filter {
+            it.description.contains(trimmed, ignoreCase = true) ||
+                it.url.contains(trimmed, ignoreCase = true)
+        }
+    }
+}

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/composer/MentionSuggestions.kt

@@ -0,0 +1,101 @@
+/*
+ * Copyright (c) 2025 Vitor Pamplona
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to use,
+ * copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the
+ * Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN
+ * AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
+ * WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+package com.vitorpamplona.amethyst.desktop.ui.chats.composer
+
+import androidx.compose.foundation.clickable
+import androidx.compose.foundation.layout.Arrangement
+import androidx.compose.foundation.layout.Column
+import androidx.compose.foundation.layout.Row
+import androidx.compose.foundation.layout.fillMaxWidth
+import androidx.compose.foundation.layout.heightIn
+import androidx.compose.foundation.layout.padding
+import androidx.compose.foundation.lazy.LazyColumn
+import androidx.compose.foundation.lazy.items
+import androidx.compose.material3.MaterialTheme
+import androidx.compose.material3.Surface
+import androidx.compose.material3.Text
+import androidx.compose.runtime.Composable
+import androidx.compose.ui.Alignment
+import androidx.compose.ui.Modifier
+import androidx.compose.ui.input.pointer.PointerIcon
+import androidx.compose.ui.input.pointer.pointerHoverIcon
+import androidx.compose.ui.text.style.TextOverflow
+import androidx.compose.ui.unit.dp
+import com.vitorpamplona.amethyst.commons.model.User
+import com.vitorpamplona.amethyst.commons.ui.components.UserAvatar
+
+/**
+ * `@mention` autocomplete dropdown for the desktop DM composer. Mirrors the
+ * note composer's mention list (ComposeNoteDialog). [onPick] receives the chosen
+ * user so the caller can insert a `nostr:npub…` reference at the caret.
+ */
+@Composable
+fun MentionSuggestions(
+    suggestions: List<User>,
+    onPick: (User) -> Unit,
+    modifier: Modifier = Modifier,
+) {
+    if (suggestions.isEmpty()) return
+
+    Surface(
+        color = MaterialTheme.colorScheme.surface,
+        shadowElevation = 4.dp,
+        modifier = modifier.fillMaxWidth(),
+    ) {
+        LazyColumn(modifier = Modifier.fillMaxWidth().heightIn(max = 200.dp)) {
+            items(suggestions, key = { it.pubkeyHex }) { user ->
+                Row(
+                    verticalAlignment = Alignment.CenterVertically,
+                    horizontalArrangement = Arrangement.spacedBy(8.dp),
+                    modifier =
+                        Modifier
+                            .fillMaxWidth()
+                            .pointerHoverIcon(PointerIcon.Hand)
+                            .clickable { onPick(user) }
+                            .padding(horizontal = 12.dp, vertical = 6.dp),
+                ) {
+                    UserAvatar(
+                        userHex = user.pubkeyHex,
+                        pictureUrl = user.profilePicture(),
+                        size = 28.dp,
+                        contentDescription = null,
+                    )
+                    Column {
+                        Text(
+                            text = user.toBestDisplayName(),
+                            style = MaterialTheme.typography.bodyMedium,
+                            color = MaterialTheme.colorScheme.onSurface,
+                            maxLines = 1,
+                            overflow = TextOverflow.Ellipsis,
+                        )
+                        Text(
+                            text = user.pubkeyNpub().take(24) + "…",
+                            style = MaterialTheme.typography.labelSmall,
+                            color = MaterialTheme.colorScheme.onSurfaceVariant,
+                            maxLines = 1,
+                            overflow = TextOverflow.Ellipsis,
+                        )
+                    }
+                }
+            }
+        }
+    }
+}

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/deck/DeckColumnContainer.kt

@@ -54,6 +54,8 @@ import androidx.compose.ui.input.key.key
 import androidx.compose.ui.input.key.onPreviewKeyEvent
 import androidx.compose.ui.input.key.type
 import androidx.compose.ui.unit.dp
+import com.vitorpamplona.amethyst.commons.model.nip30CustomEmojis.EmojiPackState
+import com.vitorpamplona.amethyst.commons.viewmodels.ChatNewMessageState
 import com.vitorpamplona.amethyst.desktop.DesktopScreen
 import com.vitorpamplona.amethyst.desktop.SettingsScreen
 import com.vitorpamplona.amethyst.desktop.account.AccountManager
@@ -79,6 +81,7 @@ import com.vitorpamplona.amethyst.desktop.ui.SearchScreen
 import com.vitorpamplona.amethyst.desktop.ui.ThreadScreen
 import com.vitorpamplona.amethyst.desktop.ui.UserProfileScreen
 import com.vitorpamplona.amethyst.desktop.ui.ZapFeedback
+import com.vitorpamplona.amethyst.desktop.ui.chats.ChatroomListState
 import com.vitorpamplona.amethyst.desktop.ui.chats.DesktopMessagesScreen
 import com.vitorpamplona.amethyst.desktop.ui.relay.RelayDashboardScreen
 import com.vitorpamplona.amethyst.desktop.ui.scheduledposts.DraftsAndScheduledScreen
@@ -398,6 +401,33 @@ internal fun RootContent(
         }
 
         DeckColumnType.Messages -> {
+            // Messages state is hoisted ABOVE the lock gate so a lock/unlock
+            // cycle (which tears down the gate's content) preserves the selected
+            // conversation and the in-progress draft.
+            val listState =
+                remember(iAccount) {
+                    ChatroomListState(iAccount, localCache, relayManager, localCache, scope)
+                }
+            val selectedRoom by listState.selectedRoom.collectAsState()
+            val emojiPacks = remember(iAccount) { EmojiPackState(iAccount.signer, localCache, scope) }
+            val messageState =
+                remember(selectedRoom) {
+                    selectedRoom?.let {
+                        ChatNewMessageState(
+                            iAccount,
+                            localCache,
+                            scope,
+                            dmInboxResolver =
+                                iAccount.dmInboxResolver?.let { resolver ->
+                                    { hexKey -> resolver.resolve(hexKey) }
+                                },
+                            emojiPacks = emojiPacks,
+                        )
+                    }
+                }
+            // Pending attachments are hoisted here too so a lock/unlock cycle
+            // doesn't drop them. Keyed on the room so switching chats starts clean.
+            val attachedFiles = remember(selectedRoom) { mutableStateListOf<java.io.File>() }
             com.vitorpamplona.amethyst.desktop.security.DesktopMessagesLockGate(
                 onOpenSettings = onNavigateToRelays,
             ) {
@@ -408,6 +438,10 @@ internal fun RootContent(
                     localCache = localCache,
                     compactMode = compactMode,
                     onNavigateToProfile = onNavigateToProfile,
+                    listState = listState,
+                    emojiPacks = emojiPacks,
+                    messageState = messageState,
+                    attachedFiles = attachedFiles,
                 )
             }
         }

desktopApp/src/jvmMain/kotlin/com/vitorpamplona/amethyst/desktop/ui/settings/ImageCompressionSettings.kt

@@ -54,6 +54,7 @@ import com.vitorpamplona.amethyst.desktop.ImageCompressionStore
 fun ImageCompressionSettings(modifier: Modifier = Modifier) {
     val quality by ImageCompressionStore.quality.collectAsState()
     val stripExif by ImageCompressionStore.stripExif.collectAsState()
+    val encryptedMediaRealType by ImageCompressionStore.encryptedMediaRealType.collectAsState()
 
     Column(modifier = modifier.fillMaxWidth()) {
         Text(
@@ -104,5 +105,40 @@ fun ImageCompressionSettings(modifier: Modifier = Modifier) {
                 onCheckedChange = ImageCompressionStore::setStripExif,
             )
         }
+
+        Spacer(Modifier.height(20.dp))
+
+        Row(
+            modifier = Modifier.fillMaxWidth(),
+            horizontalArrangement = Arrangement.SpaceBetween,
+            verticalAlignment = Alignment.CenterVertically,
+        ) {
+            Column(modifier = Modifier.weight(1f)) {
+                Text(
+                    "Reveal media type on encrypted DM uploads",
+                    style = MaterialTheme.typography.bodyMedium,
+                )
+                Spacer(Modifier.height(2.dp))
+                Text(
+                    "Off (recommended): private DM attachments upload as opaque data, so the media " +
+                        "server can't tell an image from a video or a voice note. This needs a server " +
+                        "that accepts opaque uploads — the default (nostr.download) does.\n\n" +
+                        "Turn on only if your media server rejects opaque uploads with a 415 error. " +
+                        "It declares the real file type so those servers accept the upload, at the " +
+                        "cost of the server seeing the media category (image / video / audio). File " +
+                        "contents stay encrypted either way.\n\n" +
+                        "Note: some servers (e.g. blossom.band) inspect the bytes and reject the " +
+                        "encrypted blob in BOTH modes — they can't host private DM files at all. Use " +
+                        "nostr.download for those.",
+                    style = MaterialTheme.typography.bodySmall,
+                    color = MaterialTheme.colorScheme.onSurfaceVariant,
+                )
+            }
+            Spacer(Modifier.height(0.dp))
+            Switch(
+                checked = encryptedMediaRealType,
+                onCheckedChange = ImageCompressionStore::setEncryptedMediaRealType,
+            )
+        }
     }
 }

desktopApp/src/jvmTest/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/InsertAtCursorTest.kt

@@ -0,0 +1,50 @@
+/*
+ * Copyright (c) 2025 Vitor Pamplona
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to use,
+ * copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the
+ * Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN
+ * AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
+ * WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+package com.vitorpamplona.amethyst.desktop.ui.chats
+
+import androidx.compose.ui.text.TextRange
+import androidx.compose.ui.text.input.TextFieldValue
+import kotlin.test.Test
+import kotlin.test.assertEquals
+
+class InsertAtCursorTest {
+    @Test
+    fun insertsAtCaretAndMovesCursorAfter() {
+        val result = insertAtCursor(TextFieldValue("ab", TextRange(1)), "X")
+        assertEquals("aXb", result.text)
+        assertEquals(TextRange(2), result.selection)
+    }
+
+    @Test
+    fun insertsAtEnd() {
+        val result = insertAtCursor(TextFieldValue("hi ", TextRange(3)), "🔥")
+        assertEquals("hi 🔥", result.text)
+        assertEquals(3 + "🔥".length, result.selection.start)
+    }
+
+    @Test
+    fun replacesSelection() {
+        // Selecting "bc" (range 1..3) and inserting "X" replaces the selection.
+        val result = insertAtCursor(TextFieldValue("abcd", TextRange(1, 3)), "X")
+        assertEquals("aXd", result.text)
+        assertEquals(TextRange(2), result.selection)
+    }
+}

desktopApp/src/jvmTest/kotlin/com/vitorpamplona/amethyst/desktop/ui/chats/composer/GifResultTest.kt

@@ -0,0 +1,75 @@
+/*
+ * Copyright (c) 2025 Vitor Pamplona
+ *
+ * Permission is hereby granted, free of charge, to any person obtaining a copy of
+ * this software and associated documentation files (the "Software"), to deal in
+ * the Software without restriction, including without limitation the rights to use,
+ * copy, modify, merge, publish, distribute, sublicense, and/or sell copies of the
+ * Software, and to permit persons to whom the Software is furnished to do so,
+ * subject to the following conditions:
+ *
+ * The above copyright notice and this permission notice shall be included in all
+ * copies or substantial portions of the Software.
+ *
+ * THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+ * IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY, FITNESS
+ * FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE AUTHORS OR
+ * COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN
+ * AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR IN CONNECTION
+ * WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
+ */
+package com.vitorpamplona.amethyst.desktop.ui.chats.composer
+
+import kotlin.test.Test
+import kotlin.test.assertEquals
+import kotlin.test.assertTrue
+
+class GifResultTest {
+    private fun gif(
+        url: String,
+        desc: String = "",
+    ) = GifResult(url, desc)
+
+    @Test
+    fun dedupsByUrlKeepingFirstSeenOrder() {
+        val raw =
+            listOf(
+                gif("https://host/a.gif", "cat"),
+                gif("https://host/b.gif", "dog"),
+                gif("https://host/a.gif", "cat duplicate"),
+            )
+        val result = mergeGifResults(raw, "")
+        assertEquals(2, result.size)
+        assertEquals("https://host/a.gif", result[0].url)
+        assertEquals("cat", result[0].description) // first-seen wins
+        assertEquals("https://host/b.gif", result[1].url)
+    }
+
+    @Test
+    fun blankQueryReturnsAll() {
+        val raw = listOf(gif("https://host/a.gif", "cat"), gif("https://host/b.gif", "dog"))
+        assertEquals(2, mergeGifResults(raw, "   ").size)
+    }
+
+    @Test
+    fun filtersByDescriptionCaseInsensitive() {
+        val raw = listOf(gif("https://host/a.gif", "Happy Cat"), gif("https://host/b.gif", "dog"))
+        val result = mergeGifResults(raw, "cat")
+        assertEquals(1, result.size)
+        assertEquals("https://host/a.gif", result[0].url)
+    }
+
+    @Test
+    fun filtersByUrlWhenDescriptionEmpty() {
+        val raw = listOf(gif("https://host/thumbs-up.gif", ""), gif("https://host/b.gif", "dog"))
+        val result = mergeGifResults(raw, "thumbs")
+        assertEquals(1, result.size)
+        assertTrue(result[0].url.contains("thumbs"))
+    }
+
+    @Test
+    fun noMatchReturnsEmpty() {
+        val raw = listOf(gif("https://host/a.gif", "cat"))
+        assertTrue(mergeGifResults(raw, "zebra").isEmpty())
+    }
+}

gradle/libs.versions.toml

@@ -33,6 +33,7 @@ jacksonModuleKotlin = "2.22.1"
 javaKeyring = "1.0.4"
 kmpTorRuntime = "2.6.0"
 kmpTorResource = "409.5.0"
+kodeinEmoji = "2.5.0"
 junit = "4.13.2"
 kchesslib = "1.0.5"
 kotlin = "2.4.10"
@@ -189,6 +190,7 @@ jackson-module-kotlin = { group = "com.fasterxml.jackson.module", name = "jackso
 java-keyring = { group = "com.github.javakeyring", name = "java-keyring", version.ref = "javaKeyring" }
 kmp-tor-runtime = { group = "io.matthewnelson.kmp-tor", name = "runtime", version.ref = "kmpTorRuntime" }
 kmp-tor-resource-exec-tor = { group = "io.matthewnelson.kmp-tor", name = "resource-exec-tor", version.ref = "kmpTorResource" }
+kodein-emoji-compose-m3 = { group = "org.kodein.emoji", name = "emoji-compose-m3", version.ref = "kodeinEmoji" }
 junit = { group = "junit", name = "junit", version.ref = "junit" }
 kchesslib = { module = "io.github.cvb941:kchesslib", version.ref = "kchesslib" }
 kotlinx-collections-immutable = { group = "org.jetbrains.kotlinx", name = "kotlinx-collections-immutable", version.ref = "kotlinxCollectionsImmutable" }