diff --git a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/MediaCompressor.kt b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/MediaCompressor.kt
index f984e72886..875dd72d3f 100644
--- a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/MediaCompressor.kt
+++ b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/MediaCompressor.kt
@@ -31,6 +31,7 @@ import com.vitorpamplona.quartz.utils.Log
 import id.zelory.compressor.Compressor
 import id.zelory.compressor.constraint.default
 import kotlinx.coroutines.CancellationException
+import java.io.File
 
 class MediaCompressorResult(
     val uri: Uri,
@@ -89,19 +90,23 @@ class MediaCompressor {
                 else -> 60
             }
 
+        var tempFile: File? = null
         return try {
             Log.d("MediaCompressor", "Using image compression $mediaQuality")
-            val tempFile = MediaCompressorFileUtils.from(uri, context)
+            tempFile = MediaCompressorFileUtils.from(uri, context)
             val compressedImageFile =
                 Compressor.compress(context, tempFile) {
                     default(width = 640, format = Bitmap.CompressFormat.JPEG, quality = imageQuality)
                 }
-            Log.d("MediaCompressor", "Image compression success. Original size [${tempFile.length()}], new size [${compressedImageFile.length()}]")
+            if (tempFile != compressedImageFile && !tempFile.delete()) {
+                Log.w("MediaCompressor", "Failed to delete temp file: ${tempFile.absolutePath}")
+            }
+            Log.d("MediaCompressor", "Image compression success. New size [${compressedImageFile.length()}]")
             MediaCompressorResult(compressedImageFile.toUri(), MimeTypes.IMAGE_JPEG, compressedImageFile.length())
         } catch (e: Exception) {
-            Log.d("MediaCompressor", "Image compression failed: ${e.message}")
             if (e is CancellationException) throw e
-            e.printStackTrace()
+            Log.d("MediaCompressor", "Image compression failed: ${e.message}")
+            tempFile?.delete()
             MediaCompressorResult(uri, contentType, null)
         }
     }
diff --git a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/UploadOrchestrator.kt b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/UploadOrchestrator.kt
index 0c54b765ee..b56d78932f 100644
--- a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/UploadOrchestrator.kt
+++ b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/UploadOrchestrator.kt
@@ -338,7 +338,7 @@ class UploadOrchestrator {
         try {
             val path = tempUri.path ?: return
             val file = File(path)
-            if (file.exists() && file.delete()) {
+            if (file.delete()) {
                 Log.d("UploadOrchestrator", "Deleted temp file: $path")
             }
         } catch (e: Exception) {
@@ -363,7 +363,11 @@ class UploadOrchestrator {
 
         val finalUri =
             stripAfterCompression(uri, compressed, mimeType, compressionQuality, stripMetadata, onStrippingFailed, context)
-                ?: return error(R.string.upload_cancelled)
+                ?: return error(R.string.upload_cancelled).also {
+                    deleteTempUri(compressed.uri, uri)
+                }
+
+        if (compressed.uri != finalUri) deleteTempUri(compressed.uri, uri)
 
         try {
             return when (server.type) {
@@ -372,10 +376,7 @@ class UploadOrchestrator {
                 ServerType.Blossom -> uploadBlossom(finalUri, compressed.contentType, compressed.size, alt, contentWarningReason, server.baseUrl, null, null, account, context)
             }
         } finally {
-            // Clean up intermediate temp files created by stripping and compression.
-            // Delete stripped file first (if different from compressed), then compressed (if different from original).
-            deleteTempUri(finalUri, compressed.uri)
-            deleteTempUri(compressed.uri, uri)
+            deleteTempUri(finalUri, uri)
         }
     }
 
@@ -397,9 +398,14 @@ class UploadOrchestrator {
 
         val finalUri =
             stripAfterCompression(uri, compressed, mimeType, compressionQuality, stripMetadata, onStrippingFailed, context)
-                ?: return error(R.string.upload_cancelled)
+                ?: return error(R.string.upload_cancelled).also {
+                    deleteTempUri(compressed.uri, uri)
+                }
+
+        if (compressed.uri != finalUri) deleteTempUri(compressed.uri, uri)
 
         val encrypted = EncryptFiles().encryptFile(context, finalUri, encrypt)
+        deleteTempUri(finalUri, uri)
 
         try {
             return when (server.type) {
@@ -408,10 +414,7 @@ class UploadOrchestrator {
                 ServerType.Blossom -> uploadBlossom(encrypted.uri, encrypted.contentType, encrypted.size, alt, contentWarningReason, server.baseUrl, compressed.contentType, encrypted.originalHash, account, context)
             }
         } finally {
-            // Clean up all intermediate temp files: encrypted, stripped, and compressed.
-            deleteTempUri(encrypted.uri, finalUri)
-            deleteTempUri(finalUri, compressed.uri)
-            deleteTempUri(compressed.uri, uri)
+            deleteTempUri(encrypted.uri, uri)
         }
     }
 }
diff --git a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/VideoCompressionHelper.kt b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/VideoCompressionHelper.kt
index 8f98f6fb9a..3d3c64715e 100644
--- a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/VideoCompressionHelper.kt
+++ b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/uploads/VideoCompressionHelper.kt
@@ -233,6 +233,7 @@ object VideoCompressionHelper {
 
                                     // Sanity check: compression not smaller than original
                                     if (originalSize > 0 && size >= originalSize) {
+                                        File(path).delete()
                                         applicationContext.notifyUser(
                                             "Compressed file larger than original. Using original.",
                                             Log.WARN,