diff --git a/crates/matrix-sdk/CHANGELOG.md b/crates/matrix-sdk/CHANGELOG.md
index 52e288092a8..700e86901e9 100644
--- a/crates/matrix-sdk/CHANGELOG.md
+++ b/crates/matrix-sdk/CHANGELOG.md
@@ -290,6 +290,8 @@ simpler methods:
     ([#4879](https://github.com/matrix-org/matrix-rust-sdk/pull/4879))
     - `Oidc::issuer()` was removed.
     - The `issuer` field of `UserSession` was removed.
+- `SendHandle::media_handles` was generalized into a vector
+  ([#4898](https://github.com/matrix-org/matrix-rust-sdk/pull/4898))
 
 ## [0.10.0] - 2025-02-04
 
diff --git a/crates/matrix-sdk/src/send_queue/mod.rs b/crates/matrix-sdk/src/send_queue/mod.rs
index ae746645e11..7ad431afe57 100644
--- a/crates/matrix-sdk/src/send_queue/mod.rs
+++ b/crates/matrix-sdk/src/send_queue/mod.rs
@@ -455,7 +455,7 @@ impl RoomSendQueue {
         let send_handle = SendHandle {
             room: self.clone(),
             transaction_id: transaction_id.clone(),
-            media_handles: None,
+            media_handles: vec![],
             created_at,
         };
 
@@ -1338,7 +1338,7 @@ impl QueueStorage {
                             send_handle: SendHandle {
                                 room: room.clone(),
                                 transaction_id: queued.transaction_id,
-                                media_handles: None,
+                                media_handles: vec![],
                                 created_at: queued.created_at,
                             },
                             send_error: queued.error,
@@ -1395,10 +1395,10 @@ impl QueueStorage {
                             send_handle: SendHandle {
                                 room: room.clone(),
                                 transaction_id: dep.own_transaction_id.into(),
-                                media_handles: Some(MediaHandles {
+                                media_handles: vec![MediaHandles {
                                     upload_thumbnail_txn: thumbnail_info.map(|info| info.txn),
                                     upload_file_txn: file_upload,
-                                }),
+                                }],
                                 created_at: dep.created_at,
                             },
                             send_error: None,
@@ -1911,7 +1911,7 @@ pub struct SendHandle {
     transaction_id: OwnedTransactionId,
 
     /// Additional handles for a media upload.
-    media_handles: Option<MediaHandles>,
+    media_handles: Vec<MediaHandles>,
 
     /// The time at which the event to be sent has been created.
     pub created_at: MilliSecondsSinceUnixEpoch,
@@ -1919,7 +1919,7 @@ pub struct SendHandle {
 
 impl SendHandle {
     fn nyi_for_uploads(&self) -> Result<(), RoomSendQueueStorageError> {
-        if self.media_handles.is_some() {
+        if !self.media_handles.is_empty() {
             Err(RoomSendQueueStorageError::OperationNotImplementedYet)
         } else {
             Ok(())
@@ -1936,7 +1936,7 @@ impl SendHandle {
 
         let queue = &self.room.inner.queue;
 
-        if let Some(handles) = &self.media_handles {
+        for handles in &self.media_handles {
             if queue.abort_upload(&self.transaction_id, handles).await? {
                 // Propagate a cancelled update.
                 let _ = self.room.inner.updates.send(RoomSendQueueUpdate::CancelledLocalEvent {
@@ -2069,7 +2069,7 @@ impl SendHandle {
         // one entry will be updated in the store. The other two are either
         // done, or dependent requests.
 
-        if let Some(handles) = &self.media_handles {
+        for handles in &self.media_handles {
             room.queue
                 .mark_as_unwedged(&handles.upload_file_txn)
                 .await
@@ -2166,7 +2166,7 @@ impl SendReactionHandle {
         let handle = SendHandle {
             room: self.room.clone(),
             transaction_id: self.transaction_id.clone().into(),
-            media_handles: None,
+            media_handles: vec![],
             created_at: MilliSecondsSinceUnixEpoch::now(),
         };
 
diff --git a/crates/matrix-sdk/src/send_queue/upload.rs b/crates/matrix-sdk/src/send_queue/upload.rs
index 29a09d325af..c41c3a314c0 100644
--- a/crates/matrix-sdk/src/send_queue/upload.rs
+++ b/crates/matrix-sdk/src/send_queue/upload.rs
@@ -223,7 +223,7 @@ impl RoomSendQueue {
         let send_handle = SendHandle {
             room: self.clone(),
             transaction_id: send_event_txn.clone().into(),
-            media_handles: Some(MediaHandles { upload_thumbnail_txn, upload_file_txn }),
+            media_handles: vec![MediaHandles { upload_thumbnail_txn, upload_file_txn }],
             created_at,
         };