diff --git a/lib/shared/dm-ops/process-dm-ops.js b/lib/shared/dm-ops/process-dm-ops.js
--- a/lib/shared/dm-ops/process-dm-ops.js
+++ b/lib/shared/dm-ops/process-dm-ops.js
@@ -26,6 +26,7 @@
   sendDMActionTypes,
   type SendDMOpsPayload,
 } from '../../types/dm-ops.js';
+import type { LocalMessageInfo } from '../../types/message-types.js';
 import type { RawThreadInfo } from '../../types/minimally-encoded-thread-permissions-types.js';
 import type { DispatchMetadata } from '../../types/redux-types.js';
 import type { OutboundP2PMessage } from '../../types/sqlite-types.js';
@@ -259,4 +260,37 @@
   );
 }
 
-export { useProcessDMOperation, useProcessAndSendDMOperation };
+function useRetrySendDMOperation(): (
+  messageID: string,
+  localMessageInfo: LocalMessageInfo,
+) => Promise<void> {
+  const { processOutboundMessages, getDMOpsSendingPromise } =
+    usePeerToPeerCommunication();
+  const dispatchActionPromise = useDispatchActionPromise();
+
+  return React.useCallback(
+    async (messageID: string, localMessageInfo: LocalMessageInfo) => {
+      const { promise, dmOpID } = getDMOpsSendingPromise();
+      console.log('retying');
+      processOutboundMessages(localMessageInfo.outboundP2PMessageIDs, dmOpID);
+
+      const sendingPromise: Promise<SendDMOpsPayload> = (async () => {
+        const outboundP2PMessageIDs = await promise;
+        return {
+          messageID,
+          outboundP2PMessageIDs,
+        };
+      })();
+      void dispatchActionPromise(sendDMActionTypes, sendingPromise, undefined, {
+        messageID,
+      });
+    },
+    [dispatchActionPromise, getDMOpsSendingPromise, processOutboundMessages],
+  );
+}
+
+export {
+  useProcessDMOperation,
+  useProcessAndSendDMOperation,
+  useRetrySendDMOperation,
+};
diff --git a/native/chat/failed-send.react.js b/native/chat/failed-send.react.js
--- a/native/chat/failed-send.react.js
+++ b/native/chat/failed-send.react.js
@@ -5,11 +5,16 @@
 import { Text, View } from 'react-native';
 
 import { threadInfoSelector } from 'lib/selectors/thread-selectors.js';
+import { useRetrySendDMOperation } from 'lib/shared/dm-ops/process-dm-ops.js';
 import { messageID } from 'lib/shared/message-utils.js';
 import { messageTypes } from 'lib/types/message-types-enum.js';
-import type { RawComposableMessageInfo } from 'lib/types/message-types.js';
-import { assertComposableRawMessage } from 'lib/types/message-types.js';
+import {
+  type RawComposableMessageInfo,
+  assertComposableRawMessage,
+  type LocalMessageInfo,
+} from 'lib/types/message-types.js';
 import type { ThreadInfo } from 'lib/types/minimally-encoded-thread-permissions-types.js';
+import { threadTypeIsThick } from 'lib/types/thread-types-enum.js';
 
 import { multimediaMessageSendFailed } from './multimedia-message-utils.js';
 import textMessageSendFailed from './text-message-send-failed.js';
@@ -47,6 +52,10 @@
   +styles: $ReadOnly<typeof unboundStyles>,
   +inputState: ?InputState,
   +parentThreadInfo: ?ThreadInfo,
+  +retrySendDMOperation: (
+    messageID: string,
+    localMessageInfo: LocalMessageInfo,
+  ) => Promise<void>,
 };
 class FailedSend extends React.PureComponent<Props> {
   retryingText = false;
@@ -135,6 +144,18 @@
       this.retryingMedia = true;
     }
 
+    if (threadTypeIsThick(this.props.item.threadInfo.type)) {
+      const failedMessageID = this.props.rawMessageInfo?.id;
+      invariant(failedMessageID, 'failedMessageID should be set for DMs');
+      const localMessageInfo = this.props.item.localMessageInfo;
+      invariant(
+        localMessageInfo,
+        'localMessageInfo should be set for failed message',
+      );
+      void this.props.retrySendDMOperation(failedMessageID, localMessageInfo);
+      return;
+    }
+
     const { inputState } = this.props;
     invariant(
       inputState,
@@ -163,6 +184,8 @@
     const parentThreadInfo = useSelector(state =>
       parentThreadID ? threadInfoSelector(state)[parentThreadID] : null,
     );
+    const retrySendDMOperation = useRetrySendDMOperation();
+
     return (
       <FailedSend
         {...props}
@@ -170,6 +193,7 @@
         styles={styles}
         inputState={inputState}
         parentThreadInfo={parentThreadInfo}
+        retrySendDMOperation={retrySendDMOperation}
       />
     );
   });
diff --git a/web/chat/failed-send.react.js b/web/chat/failed-send.react.js
--- a/web/chat/failed-send.react.js
+++ b/web/chat/failed-send.react.js
@@ -5,13 +5,16 @@
 
 import { type ChatMessageInfoItem } from 'lib/selectors/chat-selectors.js';
 import { threadInfoSelector } from 'lib/selectors/thread-selectors.js';
+import { useRetrySendDMOperation } from 'lib/shared/dm-ops/process-dm-ops.js';
 import { messageID } from 'lib/shared/message-utils.js';
 import { messageTypes } from 'lib/types/message-types-enum.js';
 import {
   assertComposableMessageType,
+  type LocalMessageInfo,
   type RawComposableMessageInfo,
 } from 'lib/types/message-types.js';
 import type { ThreadInfo } from 'lib/types/minimally-encoded-thread-permissions-types.js';
+import { threadTypeIsThick } from 'lib/types/thread-types-enum.js';
 
 import css from './chat-message-list.css';
 import multimediaMessageSendFailed from './multimedia-message-send-failed.js';
@@ -29,6 +32,10 @@
   +rawMessageInfo: RawComposableMessageInfo,
   +inputState: ?InputState,
   +parentThreadInfo: ?ThreadInfo,
+  +retrySendDMOperation: (
+    messageID: string,
+    localMessageInfo: LocalMessageInfo,
+  ) => Promise<void>,
 };
 class FailedSend extends React.PureComponent<Props> {
   retryingText = false;
@@ -106,6 +113,17 @@
         return;
       }
       this.retryingText = true;
+      if (threadTypeIsThick(this.props.threadInfo.type)) {
+        const failedMessageID = this.props.rawMessageInfo.id;
+        invariant(failedMessageID, 'failedMessageID should be set for DMs');
+        const localMessageInfo = this.props.item.localMessageInfo;
+        invariant(
+          localMessageInfo,
+          'localMessageInfo should be set for failed message',
+        );
+        void this.props.retrySendDMOperation(failedMessageID, localMessageInfo);
+        return;
+      }
       void inputState.sendTextMessage(
         {
           ...rawMessageInfo,
@@ -149,12 +167,15 @@
     const parentThreadInfo = useSelector(state =>
       parentThreadID ? threadInfoSelector(state)[parentThreadID] : null,
     );
+    const retrySendDMOperation = useRetrySendDMOperation();
+
     return (
       <FailedSend
         {...props}
         rawMessageInfo={rawMessageInfo}
         inputState={inputState}
         parentThreadInfo={parentThreadInfo}
+        retrySendDMOperation={retrySendDMOperation}
       />
     );
   });