diff --git a/matrix_keycloak_bot.py b/matrix_keycloak_bot.py
index 43977f5..1de8be4 100644
--- a/matrix_keycloak_bot.py
+++ b/matrix_keycloak_bot.py
@@ -9,7 +9,8 @@ from nio import (
     RoomMessageText,
     ReactionEvent,
     RoomSendResponse,
-    InviteMemberEvent
+    InviteMemberEvent,
+    OlmUnverifiedDeviceError
 )
 
 # ------------------------------------------------------------------------------
@@ -110,7 +111,7 @@ async def on_message(client: AsyncClient, room: MatrixRoom, event: RoomMessageTe
 
     parts = body.split(maxsplit=1)
     if len(parts) < 2:
-        await client.room_send(
+        await send_message_safe(
             room_id=room.room_id,
             message_type="m.room.message",
             content={"msgtype": "m.notice", "body": "Usage: !request <group_name>"},
@@ -130,9 +131,9 @@ async def on_message(client: AsyncClient, room: MatrixRoom, event: RoomMessageTe
         f"React with 👍 to **Approve** or 👎 to **Deny**."
     )
 
-    res = await client.room_send(
+    res = await send_message_safe(
+        client,
         room_id=ADMIN_ROOM_ID,
-        message_type="m.room.message",
         content={
             "msgtype": "m.text",
             "body": admin_msg_body,
@@ -151,15 +152,32 @@ async def on_message(client: AsyncClient, room: MatrixRoom, event: RoomMessageTe
         }
 
         # Confirm request receipt to the user
-        await client.room_send(
+        await send_message_safe(
+            client,
             room_id=room.room_id,
-            message_type="m.room.message",
             content={
                 "msgtype": "m.notice",
                 "body": f"Request for group '{requested_group}' submitted for admin approval.",
             },
         )
 
+async def send_message_safe(
+    client: AsyncClient, 
+    room_id: str, 
+    content: dict, 
+    message_type: str = "m.room.message"
+):
+    """Sends a message to a room, automatically trusting any unverified devices if an OlmUnverifiedDeviceError occurs."""
+    while True:
+        try:
+            return await client.room_send(
+                room_id=room_id,
+                message_type=message_type,
+                content=content,
+            )
+        except OlmUnverifiedDeviceError as e:
+            print(f"Auto-trusting unverified device '{e.device.device_id}' for user '{e.device.user_id}'...")
+            client.verify_device(e.device)
 
 async def on_reaction(client: AsyncClient, room: MatrixRoom, event: ReactionEvent):
     """Listens for reaction approvals/denials in the admin room."""
@@ -197,7 +215,7 @@ async def on_reaction(client: AsyncClient, room: MatrixRoom, event: ReactionEven
             f"🎉 Your request for access to group '{request['requested_group']}' "
             f"has been approved!" if success else f"⚠️ Approval failed: {msg}"
         )
-        await client.room_send(
+        await send_message_safe(
             room_id=request["origin_room_id"],
             message_type="m.room.message",
             content={"msgtype": "m.notice", "body": user_msg},
@@ -209,7 +227,7 @@ async def on_reaction(client: AsyncClient, room: MatrixRoom, event: ReactionEven
             f"**User:** `{request['matrix_user']}` → **Group:** `{request['requested_group']}`"
         )
 
-        await client.room_send(
+        await send_message_safe(
             room_id=request["origin_room_id"],
             message_type="m.room.message",
             content={
@@ -221,7 +239,7 @@ async def on_reaction(client: AsyncClient, room: MatrixRoom, event: ReactionEven
         return  # Ignore other reactions
 
     # Update the original admin room message to reflect resolution status
-    await client.room_send(
+    await send_message_safe(
         room_id=ADMIN_ROOM_ID,
         message_type="m.room.message",
         content={