diff --git a/lib/shared/dm-ops/process-dm-ops.js b/lib/shared/dm-ops/process-dm-ops.js
index 1939c1d17..b58dcd8e3 100644
--- a/lib/shared/dm-ops/process-dm-ops.js
+++ b/lib/shared/dm-ops/process-dm-ops.js
@@ -1,263 +1,296 @@
 // @flow
 
 import _groupBy from 'lodash/fp/groupBy.js';
 import * as React from 'react';
 import uuid from 'uuid';
 
 import { dmOpSpecs } from './dm-op-specs.js';
 import type {
   OutboundDMOperationSpecification,
   DMOperationSpecification,
 } from './dm-op-utils.js';
 import {
   createMessagesToPeersFromDMOp,
   dmOperationSpecificationTypes,
 } from './dm-op-utils.js';
 import { useLoggedInUserInfo } from '../../hooks/account-hooks.js';
 import { useGetLatestMessageEdit } from '../../hooks/latest-message-edit.js';
 import { useDispatchWithMetadata } from '../../hooks/ops-hooks.js';
 import { mergeUpdatesWithMessageInfos } from '../../reducers/message-reducer.js';
 import { getAllPeerUserIDAndDeviceIDs } from '../../selectors/user-selectors.js';
 import { usePeerToPeerCommunication } from '../../tunnelbroker/peer-to-peer-context.js';
 import {
   processDMOpsActionType,
   queueDMOpsActionType,
   sendDMActionTypes,
   type SendDMOpsSuccessPayload,
 } 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';
 import { threadTypes } from '../../types/thread-types-enum.js';
 import type { LegacyRawThreadInfo } from '../../types/thread-types.js';
 import { updateTypes } from '../../types/update-types-enum.js';
 import { useDispatchActionPromise } from '../../utils/redux-promise-utils.js';
 import { useSelector } from '../../utils/redux-utils.js';
 import { messageSpecs } from '../messages/message-specs.js';
 import { updateSpecs } from '../updates/update-specs.js';
 
 function useProcessDMOperation(): (
   dmOperationSpecification: DMOperationSpecification,
   dmOpID: ?string,
 ) => Promise<void> {
   const fetchMessage = useGetLatestMessageEdit();
   const threadInfos = useSelector(state => state.threadStore.threadInfos);
 
   const utilities = React.useMemo(
     () => ({
       fetchMessage,
       threadInfos,
     }),
     [fetchMessage, threadInfos],
   );
 
   const dispatchWithMetadata = useDispatchWithMetadata();
   const loggedInUserInfo = useLoggedInUserInfo();
   const viewerID = loggedInUserInfo?.id;
   const allPeerUserIDAndDeviceIDs = useSelector(getAllPeerUserIDAndDeviceIDs);
   const currentUserInfo = useSelector(state => state.currentUserInfo);
 
   return React.useCallback(
     async (
       dmOperationSpecification: DMOperationSpecification,
       dmOpID: ?string,
     ) => {
       if (!viewerID) {
         console.log('ignored DMOperation because logged out');
         return;
       }
 
       let outboundP2PMessages: ?$ReadOnlyArray<OutboundP2PMessage> = null;
       if (
         dmOperationSpecification.type === dmOperationSpecificationTypes.OUTBOUND
       ) {
         outboundP2PMessages = await createMessagesToPeersFromDMOp(
           dmOperationSpecification,
           allPeerUserIDAndDeviceIDs,
           currentUserInfo,
         );
       }
 
       let dispatchMetadata: ?DispatchMetadata = null;
       if (
         dmOperationSpecification.type ===
           dmOperationSpecificationTypes.OUTBOUND &&
         dmOpID
       ) {
         dispatchMetadata = {
           dmOpID,
         };
       } else if (
         dmOperationSpecification.type === dmOperationSpecificationTypes.INBOUND
       ) {
         dispatchMetadata = dmOperationSpecification.metadata;
       }
 
       const { op: dmOp } = dmOperationSpecification;
       const processingCheckResult = dmOpSpecs[dmOp.type].canBeProcessed(
         dmOp,
         viewerID,
         utilities,
       );
       if (!processingCheckResult.isProcessingPossible) {
         if (processingCheckResult.reason.type === 'missing_thread') {
           dispatchWithMetadata(
             {
               type: queueDMOpsActionType,
               payload: {
                 operation: dmOp,
                 threadID: processingCheckResult.reason.threadID,
                 timestamp: Date.now(),
               },
             },
             dispatchMetadata,
           );
         }
         return;
       }
       const { rawMessageInfos, updateInfos } = await dmOpSpecs[
         dmOp.type
       ].processDMOperation(dmOp, viewerID, utilities);
 
       const { rawMessageInfos: allNewMessageInfos } =
         mergeUpdatesWithMessageInfos(rawMessageInfos, updateInfos);
       const messagesByThreadID = _groupBy(message => message.threadID)(
         allNewMessageInfos,
       );
 
       const updatedThreadInfosByThreadID: {
         [string]: RawThreadInfo | LegacyRawThreadInfo,
       } = {};
       for (const threadID in messagesByThreadID) {
         updatedThreadInfosByThreadID[threadID] = threadInfos[threadID];
       }
       for (const update of updateInfos) {
         const updatedThreadInfo = updateSpecs[
           update.type
         ].getUpdatedThreadInfo?.(update, updatedThreadInfosByThreadID);
         if (
           updatedThreadInfo &&
           updatedThreadInfo?.type === threadTypes.THICK_SIDEBAR
         ) {
           updatedThreadInfosByThreadID[updatedThreadInfo.id] =
             updatedThreadInfo;
         }
       }
 
       for (const threadID in messagesByThreadID) {
         const repliesCountIncreasingMessages = messagesByThreadID[
           threadID
         ].filter(message => messageSpecs[message.type].includedInRepliesCount);
         if (repliesCountIncreasingMessages.length > 0) {
           const threadInfo = updatedThreadInfosByThreadID[threadID];
           const repliesCountIncreaseTime = Math.max(
             repliesCountIncreasingMessages.map(message => message.time),
           );
           updateInfos.push({
             type: updateTypes.UPDATE_THREAD,
             id: uuid.v4(),
             time: repliesCountIncreaseTime,
             threadInfo: {
               ...threadInfo,
               repliesCount:
                 threadInfo.repliesCount + repliesCountIncreasingMessages.length,
             },
           });
         }
 
         const messagesFromOtherPeers = messagesByThreadID[threadID].filter(
           message => message.creatorID !== viewerID,
         );
         if (messagesFromOtherPeers.length === 0) {
           continue;
         }
         // We take the most recent timestamp to make sure that updates older
         // than it won't flip the status to read.
         const time = Math.max(
           messagesFromOtherPeers.map(message => message.time),
         );
         updateInfos.push({
           type: updateTypes.UPDATE_THREAD_READ_STATUS,
           id: uuid.v4(),
           time,
           threadID,
           unread: true,
         });
       }
 
       let messageIDWithoutAutoRetry: ?string = null;
       if (
         dmOperationSpecification.type ===
           dmOperationSpecificationTypes.OUTBOUND &&
         !dmOpSpecs[dmOperationSpecification.op.type].supportsAutoRetry
       ) {
         messageIDWithoutAutoRetry = dmOperationSpecification.op.messageID;
       }
 
       dispatchWithMetadata(
         {
           type: processDMOpsActionType,
           payload: {
             rawMessageInfos,
             updateInfos,
             outboundP2PMessages,
             messageIDWithoutAutoRetry,
           },
         },
         dispatchMetadata,
       );
     },
     [
       viewerID,
       utilities,
       dispatchWithMetadata,
       allPeerUserIDAndDeviceIDs,
       currentUserInfo,
       threadInfos,
     ],
   );
 }
 
 function useProcessAndSendDMOperation(): (
   dmOperationSpecification: OutboundDMOperationSpecification,
 ) => Promise<void> {
   const processDMOps = useProcessDMOperation();
   const dispatchActionPromise = useDispatchActionPromise();
   const { getDMOpsSendingPromise } = usePeerToPeerCommunication();
 
   return React.useCallback(
     async (dmOperationSpecification: OutboundDMOperationSpecification) => {
       const { promise, dmOpID } = getDMOpsSendingPromise();
       await processDMOps(dmOperationSpecification, dmOpID);
 
       if (
         dmOperationSpecification.type ===
           dmOperationSpecificationTypes.OUTBOUND &&
         !dmOpSpecs[dmOperationSpecification.op.type].supportsAutoRetry &&
         dmOperationSpecification.op.messageID
       ) {
         const messageID: string = dmOperationSpecification.op.messageID;
 
         const sendingPromise: Promise<SendDMOpsSuccessPayload> = (async () => {
           const outboundP2PMessageIDs = await promise;
           return {
             messageID,
             outboundP2PMessageIDs,
           };
         })();
 
         void dispatchActionPromise(
           sendDMActionTypes,
           sendingPromise,
           undefined,
           {
             messageID,
           },
         );
       }
     },
     [dispatchActionPromise, getDMOpsSendingPromise, processDMOps],
   );
 }
 
-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();
+      processOutboundMessages(localMessageInfo.outboundP2PMessageIDs, dmOpID);
+
+      const sendingPromise: Promise<SendDMOpsSuccessPayload> = (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
index a1da3bb00..c738c4a26 100644
--- a/native/chat/failed-send.react.js
+++ b/native/chat/failed-send.react.js
@@ -1,177 +1,201 @@
 // @flow
 
 import invariant from 'invariant';
 import * as React from 'react';
 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';
 import Button from '../components/button.react.js';
 import { type InputState, InputStateContext } from '../input/input-state.js';
 import { useSelector } from '../redux/redux-utils.js';
 import { useStyles } from '../themes/colors.js';
 import type { ChatMessageInfoItemWithHeight } from '../types/chat-types.js';
 
 const failedSendHeight = 22;
 
 const unboundStyles = {
   deliveryFailed: {
     color: 'listSeparatorLabel',
     paddingHorizontal: 3,
   },
   failedSendInfo: {
     flex: 1,
     flexDirection: 'row',
     justifyContent: 'flex-end',
     marginRight: 20,
     paddingTop: 5,
   },
   retrySend: {
     paddingHorizontal: 3,
   },
 };
 
 type BaseProps = {
   +item: ChatMessageInfoItemWithHeight,
 };
 type Props = {
   ...BaseProps,
   +rawMessageInfo: ?RawComposableMessageInfo,
   +styles: $ReadOnly<typeof unboundStyles>,
   +inputState: ?InputState,
   +parentThreadInfo: ?ThreadInfo,
+  +retrySendDMOperation: (
+    messageID: string,
+    localMessageInfo: LocalMessageInfo,
+  ) => Promise<void>,
 };
 class FailedSend extends React.PureComponent<Props> {
   retryingText = false;
   retryingMedia = false;
 
   componentDidUpdate(prevProps: Props) {
     const newItem = this.props.item;
     const prevItem = prevProps.item;
     if (
       newItem.messageShapeType === 'multimedia' &&
       prevItem.messageShapeType === 'multimedia'
     ) {
       const isFailed = multimediaMessageSendFailed(newItem);
       const wasFailed = multimediaMessageSendFailed(prevItem);
       const isDone =
         newItem.messageInfo.id !== null && newItem.messageInfo.id !== undefined;
       const wasDone =
         prevItem.messageInfo.id !== null &&
         prevItem.messageInfo.id !== undefined;
       if ((isFailed && !wasFailed) || (isDone && !wasDone)) {
         this.retryingMedia = false;
       }
     } else if (
       newItem.messageShapeType === 'text' &&
       prevItem.messageShapeType === 'text'
     ) {
       const isFailed = textMessageSendFailed(newItem);
       const wasFailed = textMessageSendFailed(prevItem);
       const isDone =
         newItem.messageInfo.id !== null && newItem.messageInfo.id !== undefined;
       const wasDone =
         prevItem.messageInfo.id !== null &&
         prevItem.messageInfo.id !== undefined;
       if ((isFailed && !wasFailed) || (isDone && !wasDone)) {
         this.retryingText = false;
       }
     }
   }
 
   render(): React.Node {
     if (!this.props.rawMessageInfo) {
       return null;
     }
     const threadColor = {
       color: `#${this.props.item.threadInfo.color}`,
     };
 
     return (
       <View style={this.props.styles.failedSendInfo}>
         <Text style={this.props.styles.deliveryFailed} numberOfLines={1}>
           DELIVERY FAILED.
         </Text>
         <Button onPress={this.retrySend}>
           <Text
             style={{
               ...this.props.styles.retrySend,
               ...threadColor,
             }}
             numberOfLines={1}
           >
             {'RETRY?'}
           </Text>
         </Button>
       </View>
     );
   }
 
   retrySend = () => {
     const { rawMessageInfo } = this.props;
     if (!rawMessageInfo) {
       return;
     }
 
     if (rawMessageInfo.type === messageTypes.TEXT) {
       if (this.retryingText) {
         return;
       }
       this.retryingText = true;
     } else if (
       rawMessageInfo.type === messageTypes.IMAGES ||
       rawMessageInfo.type === messageTypes.MULTIMEDIA
     ) {
       if (this.retryingMedia) {
         return;
       }
       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,
       'inputState should be initialized before user can hit retry',
     );
     const { localID } = rawMessageInfo;
     invariant(localID, 'failed RawMessageInfo should have localID');
     void inputState.retryMessage(
       localID,
       this.props.item.threadInfo,
       this.props.parentThreadInfo,
     );
   };
 }
 
 const ConnectedFailedSend: React.ComponentType<BaseProps> =
   React.memo<BaseProps>(function ConnectedFailedSend(props: BaseProps) {
     const id = messageID(props.item.messageInfo);
     const rawMessageInfo = useSelector(state => {
       const message = state.messageStore.messages[id];
       return message ? assertComposableRawMessage(message) : null;
     });
     const styles = useStyles(unboundStyles);
     const inputState = React.useContext(InputStateContext);
     const { parentThreadID } = props.item.threadInfo;
     const parentThreadInfo = useSelector(state =>
       parentThreadID ? threadInfoSelector(state)[parentThreadID] : null,
     );
+    const retrySendDMOperation = useRetrySendDMOperation();
+
     return (
       <FailedSend
         {...props}
         rawMessageInfo={rawMessageInfo}
         styles={styles}
         inputState={inputState}
         parentThreadInfo={parentThreadInfo}
+        retrySendDMOperation={retrySendDMOperation}
       />
     );
   });
 
 export { ConnectedFailedSend as FailedSend, failedSendHeight };
diff --git a/web/chat/failed-send.react.js b/web/chat/failed-send.react.js
index 17630977e..9fe247a9e 100644
--- a/web/chat/failed-send.react.js
+++ b/web/chat/failed-send.react.js
@@ -1,162 +1,183 @@
 // @flow
 
 import invariant from 'invariant';
 import * as React from 'react';
 
 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';
 import textMessageSendFailed from './text-message-send-failed.js';
 import Button from '../components/button.react.js';
 import { type InputState, InputStateContext } from '../input/input-state.js';
 import { useSelector } from '../redux/redux-utils.js';
 
 type BaseProps = {
   +item: ChatMessageInfoItem,
   +threadInfo: ThreadInfo,
 };
 type Props = {
   ...BaseProps,
   +rawMessageInfo: RawComposableMessageInfo,
   +inputState: ?InputState,
   +parentThreadInfo: ?ThreadInfo,
+  +retrySendDMOperation: (
+    messageID: string,
+    localMessageInfo: LocalMessageInfo,
+  ) => Promise<void>,
 };
 class FailedSend extends React.PureComponent<Props> {
   retryingText = false;
   retryingMedia = false;
 
   componentDidUpdate(prevProps: Props) {
     if (
       (this.props.rawMessageInfo.type === messageTypes.IMAGES ||
         this.props.rawMessageInfo.type === messageTypes.MULTIMEDIA) &&
       (prevProps.rawMessageInfo.type === messageTypes.IMAGES ||
         prevProps.rawMessageInfo.type === messageTypes.MULTIMEDIA)
     ) {
       const { inputState } = this.props;
       const prevInputState = prevProps.inputState;
       invariant(
         inputState && prevInputState,
         'inputState should be set in FailedSend',
       );
       const isFailed = multimediaMessageSendFailed(this.props.item, inputState);
       const wasFailed = multimediaMessageSendFailed(
         prevProps.item,
         prevInputState,
       );
       const isDone =
         this.props.item.messageInfo.id !== null &&
         this.props.item.messageInfo.id !== undefined;
       const wasDone =
         prevProps.item.messageInfo.id !== null &&
         prevProps.item.messageInfo.id !== undefined;
       if ((isFailed && !wasFailed) || (isDone && !wasDone)) {
         this.retryingMedia = false;
       }
     } else if (
       this.props.rawMessageInfo.type === messageTypes.TEXT &&
       prevProps.rawMessageInfo.type === messageTypes.TEXT
     ) {
       const isFailed = textMessageSendFailed(this.props.item);
       const wasFailed = textMessageSendFailed(prevProps.item);
       const isDone =
         this.props.item.messageInfo.id !== null &&
         this.props.item.messageInfo.id !== undefined;
       const wasDone =
         prevProps.item.messageInfo.id !== null &&
         prevProps.item.messageInfo.id !== undefined;
       if ((isFailed && !wasFailed) || (isDone && !wasDone)) {
         this.retryingText = false;
       }
     }
   }
 
   render(): React.Node {
     return (
       <div className={css.failedSend}>
         <span className={css.deliveryFailed}>Delivery failed.</span>
         <Button
           variant="text"
           buttonColor={{
             color: `#${this.props.threadInfo.color}`,
           }}
           onClick={this.retrySend}
         >
           <span className={css.retryButtonText}>Retry?</span>
         </Button>
       </div>
     );
   }
 
   retrySend = () => {
     const { inputState } = this.props;
     invariant(inputState, 'inputState should be set in FailedSend');
 
     const { rawMessageInfo } = this.props;
     if (rawMessageInfo.type === messageTypes.TEXT) {
       if (this.retryingText) {
         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,
           time: Date.now(),
         },
         this.props.threadInfo,
         this.props.parentThreadInfo,
       );
     } else if (
       rawMessageInfo.type === messageTypes.IMAGES ||
       rawMessageInfo.type === messageTypes.MULTIMEDIA
     ) {
       const { localID } = rawMessageInfo;
       invariant(localID, 'failed RawMessageInfo should have localID');
       if (this.retryingMedia) {
         return;
       }
       this.retryingMedia = true;
       inputState.retryMultimediaMessage(localID, this.props.threadInfo);
     }
   };
 }
 
 const ConnectedFailedSend: React.ComponentType<BaseProps> =
   React.memo<BaseProps>(function ConnectedFailedSend(props) {
     const { messageInfo } = props.item;
     assertComposableMessageType(messageInfo.type);
     const id = messageID(messageInfo);
     const rawMessageInfo = useSelector(
       state => state.messageStore.messages[id],
     );
     assertComposableMessageType(rawMessageInfo.type);
     invariant(
       rawMessageInfo.type === messageTypes.TEXT ||
         rawMessageInfo.type === messageTypes.IMAGES ||
         rawMessageInfo.type === messageTypes.MULTIMEDIA,
       'FailedSend should only be used for composable message types',
     );
     const inputState = React.useContext(InputStateContext);
     const { parentThreadID } = props.threadInfo;
     const parentThreadInfo = useSelector(state =>
       parentThreadID ? threadInfoSelector(state)[parentThreadID] : null,
     );
+    const retrySendDMOperation = useRetrySendDMOperation();
+
     return (
       <FailedSend
         {...props}
         rawMessageInfo={rawMessageInfo}
         inputState={inputState}
         parentThreadInfo={parentThreadInfo}
+        retrySendDMOperation={retrySendDMOperation}
       />
     );
   });
 
 export default ConnectedFailedSend;