diff --git a/desktopApp/src/jvmTest/kotlin/com/vitorpamplona/amethyst/desktop/cache/CoordinatorPipelineTest.kt b/desktopApp/src/jvmTest/kotlin/com/vitorpamplona/amethyst/desktop/cache/CoordinatorPipelineTest.kt
index a43b3758e6..480ea4fe06 100644
--- a/desktopApp/src/jvmTest/kotlin/com/vitorpamplona/amethyst/desktop/cache/CoordinatorPipelineTest.kt
+++ b/desktopApp/src/jvmTest/kotlin/com/vitorpamplona/amethyst/desktop/cache/CoordinatorPipelineTest.kt
@@ -127,6 +127,8 @@ class CoordinatorPipelineTest {
         override fun activeCounts(url: NormalizedRelayUrl): Map<String, List<Filter>> = emptyMap()
 
         override fun activeOutboxCache(url: NormalizedRelayUrl): Set<HexKey> = emptySet()
+
+        override fun activeOutboxEvents(url: NormalizedRelayUrl): List<Event> = emptyList()
     }
 
     private fun createCoordinator(
diff --git a/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/INostrClient.kt b/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/INostrClient.kt
index 125643864e..35a09a9748 100644
--- a/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/INostrClient.kt
+++ b/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/INostrClient.kt
@@ -104,6 +104,9 @@ interface INostrClient : AutoCloseable {
     fun activeCounts(url: NormalizedRelayUrl): Map<String, List<Filter>>
 
     fun activeOutboxCache(url: NormalizedRelayUrl): Set<HexKey>
+
+    /** The events still pending delivery to [url] (full events, not just ids). */
+    fun activeOutboxEvents(url: NormalizedRelayUrl): List<Event>
 }
 
 class EmptyNostrClient : INostrClient {
@@ -158,5 +161,7 @@ class EmptyNostrClient : INostrClient {
 
     override fun activeOutboxCache(url: NormalizedRelayUrl): Set<HexKey> = emptySet()
 
+    override fun activeOutboxEvents(url: NormalizedRelayUrl): List<Event> = emptyList()
+
     override fun close() {}
 }
diff --git a/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/NostrClient.kt b/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/NostrClient.kt
index 6516d0cb5b..073575d7e5 100644
--- a/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/NostrClient.kt
+++ b/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/NostrClient.kt
@@ -369,6 +369,8 @@ class NostrClient(
 
     override fun activeOutboxCache(url: NormalizedRelayUrl): Set<HexKey> = eventOutbox.activeOutboxCacheFor(url)
 
+    override fun activeOutboxEvents(url: NormalizedRelayUrl): List<Event> = eventOutbox.activeOutboxEventsFor(url)
+
     override fun pendingPublishRelaysFor(eventId: HexKey): Set<NormalizedRelayUrl>? = eventOutbox.pendingRelaysFor(eventId)
 
     override fun getReqFiltersOrNull(subId: String): Map<NormalizedRelayUrl, List<Filter>>? = activeRequests.getSubscriptionFiltersOrNull(subId)
diff --git a/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/pool/PoolEventOutbox.kt b/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/pool/PoolEventOutbox.kt
index 0e4506a842..9547e9e453 100644
--- a/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/pool/PoolEventOutbox.kt
+++ b/quartz/src/commonMain/kotlin/com/vitorpamplona/quartz/nip01Core/relay/client/pool/PoolEventOutbox.kt
@@ -96,6 +96,21 @@ class PoolEventOutbox {
         return myEvents
     }
 
+    /**
+     * The events still pending delivery to [url]. Unlike [activeOutboxCacheFor] (ids only), this
+     * returns the full events so callers can inspect kind/tags — e.g. to explain *why* a relay is
+     * being authenticated with (a pending gift wrap => sending a DM to its recipient).
+     */
+    fun activeOutboxEventsFor(url: NormalizedRelayUrl): List<Event> {
+        val myEvents = mutableListOf<Event>()
+        eventOutbox.forEach { (_, outboxCache) ->
+            if (url in outboxCache.relaysRemaining) {
+                myEvents.add(outboxCache.event)
+            }
+        }
+        return myEvents
+    }
+
     /**
      * Returns the relays that have NOT yet acknowledged [eventId] with an OK, or
      * null if the event is not currently tracked (never sent or already fully done).
diff --git a/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/NostrSignerRemoteIsolationTest.kt b/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/NostrSignerRemoteIsolationTest.kt
index f7213b655f..f86af44b03 100644
--- a/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/NostrSignerRemoteIsolationTest.kt
+++ b/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/NostrSignerRemoteIsolationTest.kt
@@ -104,6 +104,8 @@ private class TrackingNostrClient : INostrClient {
 
     override fun activeOutboxCache(url: NormalizedRelayUrl): Set<String> = emptySet()
 
+    override fun activeOutboxEvents(url: NormalizedRelayUrl): List<Event> = emptyList()
+
     override fun close() {}
 }
 
diff --git a/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/RemoteSignerManagerRetryTest.kt b/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/RemoteSignerManagerRetryTest.kt
index 3f346531b8..77ca2c5d3c 100644
--- a/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/RemoteSignerManagerRetryTest.kt
+++ b/quartz/src/commonTest/kotlin/com/vitorpamplona/quartz/nip46RemoteSigner/signer/RemoteSignerManagerRetryTest.kt
@@ -431,6 +431,8 @@ private class CapturingNostrClient : INostrClient {
 
     override fun activeOutboxCache(url: NormalizedRelayUrl): Set<HexKey> = emptySet()
 
+    override fun activeOutboxEvents(url: NormalizedRelayUrl): List<Event> = emptyList()
+
     override fun close() {}
 }
 
@@ -490,5 +492,7 @@ private class CountingNostrClient(
 
     override fun activeOutboxCache(url: NormalizedRelayUrl): Set<HexKey> = emptySet()
 
+    override fun activeOutboxEvents(url: NormalizedRelayUrl): List<Event> = emptyList()
+
     override fun close() {}
 }