diff --git a/matrix_sdk/src/client.rs b/matrix_sdk/src/client.rs
index 8d76ef22..403954f0 100644
--- a/matrix_sdk/src/client.rs
+++ b/matrix_sdk/src/client.rs
@@ -1057,7 +1057,15 @@ impl Client {
                 if self.base_client.should_share_group_session(room_id).await {
                     // TODO we need to make sure that only one such request is
                     // in flight per room at a time.
-                    self.share_group_session(room_id).await?;
+                    let response = self.share_group_session(room_id).await;
+
+                    // If one of the responses failed invalidate the group
+                    // session as using it would end up in undecryptable
+                    // messages.
+                    if let Err(r) = response {
+                        self.base_client.invalidate_group_session(room_id).await;
+                        return Err(r);
+                    }
                 }
 
                 raw_content = serde_json::value::to_raw_value(
diff --git a/matrix_sdk_base/src/client.rs b/matrix_sdk_base/src/client.rs
index 0f8826c5..ab807239 100644
--- a/matrix_sdk_base/src/client.rs
+++ b/matrix_sdk_base/src/client.rs
@@ -1087,6 +1087,22 @@ impl BaseClient {
         Ok(())
     }
 
+    /// Invalidate the currently active outbound group session for the given
+    /// room.
+    ///
+    /// Returns true if a session was invalidated, false if there was no session
+    /// to invalidate.
+    #[cfg(feature = "encryption")]
+    #[cfg_attr(docsrs, doc(cfg(feature = "encryption")))]
+    pub async fn invalidate_group_session(&self, room_id: &RoomId) -> bool {
+        let mut olm = self.olm.lock().await;
+
+        match &mut *olm {
+            Some(o) => o.invalidate_group_session(room_id),
+            None => false,
+        }
+    }
+
     pub(crate) async fn emit_timeline_event(
         &self,
         room_id: &RoomId,
@@ -1586,4 +1602,24 @@ mod test {
         let room = client.get_joined_room(&room_id).await;
         assert!(room.is_some());
     }
+
+    #[async_test]
+    async fn test_group_session_invalidation() {
+        let client = get_client();
+        let room_id = get_room_id();
+
+        let mut sync_response = EventBuilder::default()
+            .add_room_event(EventsFile::Member, RoomEvent::RoomMember)
+            .build_sync_response();
+
+        client
+            .receive_sync_response(&mut sync_response)
+            .await
+            .unwrap();
+
+        assert!(client.should_share_group_session(&room_id).await);
+        let _ = client.share_group_session(&room_id).await.unwrap();
+        assert!(!client.should_share_group_session(&room_id).await);
+        client.invalidate_group_session(&room_id).await;
+    }
 }
diff --git a/matrix_sdk_crypto/src/machine.rs b/matrix_sdk_crypto/src/machine.rs
index 96a3b897..c55e1bc3 100644
--- a/matrix_sdk_crypto/src/machine.rs
+++ b/matrix_sdk_crypto/src/machine.rs
@@ -1219,6 +1219,15 @@ impl OlmMachine {
         }
     }
 
+    /// Invalidate the currently active outbound group session for the given
+    /// room.
+    ///
+    /// Returns true if a session was invalidated, false if there was no session
+    /// to invalidate.
+    pub fn invalidate_group_session(&mut self, room_id: &RoomId) -> bool {
+        self.outbound_group_sessions.remove(room_id).is_some()
+    }
+
     // TODO accept an algorithm here
     /// Get to-device requests to share a group session with users in a room.
     ///
@@ -1816,6 +1825,22 @@ mod test {
         assert!(ret.is_ok());
     }
 
+    #[tokio::test]
+    async fn tests_session_invalidation() {
+        let mut machine = OlmMachine::new(&user_id(), DEVICE_ID);
+        let room_id = RoomId::try_from("!test:example.org").unwrap();
+
+        machine
+            .create_outbound_group_session(&room_id)
+            .await
+            .unwrap();
+        assert!(machine.outbound_group_sessions.get(&room_id).is_some());
+
+        machine.invalidate_group_session(&room_id);
+
+        assert!(machine.outbound_group_sessions.get(&room_id).is_none());
+    }
+
     #[tokio::test]
     async fn test_invalid_signature() {
         let machine = OlmMachine::new(&user_id(), DEVICE_ID);