diff --git a/src/components/dms/MessageItem.tsx b/src/components/dms/MessageItem.tsx
index cafd7ca5a5..f456fa4748 100644
--- a/src/components/dms/MessageItem.tsx
+++ b/src/components/dms/MessageItem.tsx
@@ -202,7 +202,7 @@ let MessageItemMetadata = ({
         )}
       </TimeElapsed>
 
-      {item.type === 'pending-message' && item.retry && (
+      {item.type === 'pending-message' && item.failed && (
         <>
           {' '}
           &middot;{' '}
@@ -214,15 +214,20 @@ let MessageItemMetadata = ({
               },
             ]}>
             {_(msg`Failed to send`)}
-          </Text>{' '}
-          &middot;{' '}
-          <InlineLinkText
-            label={_(msg`Click to retry failed message`)}
-            to="#"
-            onPress={handleRetry}
-            style={[a.text_xs]}>
-            {_(msg`Retry`)}
-          </InlineLinkText>
+          </Text>
+          {item.retry && (
+            <>
+              {' '}
+              &middot;{' '}
+              <InlineLinkText
+                label={_(msg`Click to retry failed message`)}
+                to="#"
+                onPress={handleRetry}
+                style={[a.text_xs]}>
+                {_(msg`Retry`)}
+              </InlineLinkText>
+            </>
+          )}
         </>
       )}
     </Text>
diff --git a/src/screens/Messages/Conversation/MessageListError.tsx b/src/screens/Messages/Conversation/MessageListError.tsx
index c6e246a3fb..1e0dc34747 100644
--- a/src/screens/Messages/Conversation/MessageListError.tsx
+++ b/src/screens/Messages/Conversation/MessageListError.tsx
@@ -10,22 +10,21 @@ import {ArrowRotateCounterClockwise_Stroke2_Corner0_Rounded as Refresh} from '#/
 import {CircleInfo_Stroke2_Corner0_Rounded as CircleInfo} from '#/components/icons/CircleInfo'
 import {Text} from '#/components/Typography'
 
-export function MessageListError({
-  item,
-}: {
-  item: ConvoItem & {type: 'error-recoverable'}
-}) {
+export function MessageListError({item}: {item: ConvoItem & {type: 'error'}}) {
   const t = useTheme()
   const {_} = useLingui()
   const message = React.useMemo(() => {
     return {
-      [ConvoItemError.Network]: _(
-        msg`There was an issue connecting to the chat.`,
+      [ConvoItemError.Unknown]: _(
+        msg`An unknown error occurred. If the issue persists, contact support.`,
       ),
       [ConvoItemError.FirehoseFailed]: _(
         msg`This chat was disconnected due to a network error.`,
       ),
       [ConvoItemError.HistoryFailed]: _(msg`Failed to load past messages.`),
+      [ConvoItemError.UserBlocked]: _(
+        msg`The other user in this chat has blocked you.`,
+      ),
     }[item.code]
   }, [_, item.code])
 
@@ -49,24 +48,26 @@ export function MessageListError({
             fill={t.palette.negative_400}
             style={[{top: 3}]}
           />
-          <View style={[a.flex_1, {maxWidth: 200}]}>
+          <View style={[a.flex_1, {maxWidth: 240}]}>
             <Text style={[a.leading_snug]}>{message}</Text>
           </View>
         </View>
 
-        <Button
-          label={_(msg`Press to retry`)}
-          size="small"
-          variant="ghost"
-          color="secondary"
-          onPress={e => {
-            e.preventDefault()
-            item.retry()
-            return false
-          }}>
-          <ButtonText>{_(msg`Retry`)}</ButtonText>
-          <ButtonIcon icon={Refresh} position="right" />
-        </Button>
+        {item.retry && (
+          <Button
+            label={_(msg`Press to retry`)}
+            size="small"
+            variant="ghost"
+            color="secondary"
+            onPress={e => {
+              e.preventDefault()
+              item.retry?.()
+              return false
+            }}>
+            <ButtonText>{_(msg`Retry`)}</ButtonText>
+            <ButtonIcon icon={Refresh} position="right" />
+          </Button>
+        )}
       </View>
     </View>
   )
diff --git a/src/screens/Messages/Conversation/MessagesList.tsx b/src/screens/Messages/Conversation/MessagesList.tsx
index 9c7774e578..bb65567a27 100644
--- a/src/screens/Messages/Conversation/MessagesList.tsx
+++ b/src/screens/Messages/Conversation/MessagesList.tsx
@@ -39,7 +39,7 @@ function renderItem({item}: {item: ConvoItem}) {
     return <MessageItem item={item} />
   } else if (item.type === 'deleted-message') {
     return <Text>Deleted message</Text>
-  } else if (item.type === 'error-recoverable') {
+  } else if (item.type === 'error') {
     return <MessageListError item={item} />
   }
 
diff --git a/src/state/messages/convo/agent.ts b/src/state/messages/convo/agent.ts
index 94bb8dda44..8946a786c6 100644
--- a/src/state/messages/convo/agent.ts
+++ b/src/state/messages/convo/agent.ts
@@ -5,6 +5,8 @@ import {
   ChatBskyConvoGetLog,
   ChatBskyConvoSendMessage,
 } from '@atproto/api'
+import {XRPCError} from '@atproto/xrpc'
+import EventEmitter from 'eventemitter3'
 import {nanoid} from 'nanoid/non-secure'
 
 import {networkRetry} from '#/lib/async/retry'
@@ -14,11 +16,13 @@ import {
   ACTIVE_POLL_INTERVAL,
   BACKGROUND_POLL_INTERVAL,
   INACTIVE_TIMEOUT,
+  NETWORK_FAILURE_STATUSES,
 } from '#/state/messages/convo/const'
 import {
   ConvoDispatch,
   ConvoDispatchEvent,
   ConvoErrorCode,
+  ConvoEvent,
   ConvoItem,
   ConvoItemError,
   ConvoParams,
@@ -82,6 +86,8 @@ export class Convo {
 
   private lastActiveTimestamp: number | undefined
 
+  private emitter = new EventEmitter<{event: [ConvoEvent]}>()
+
   convoId: string
   convo: ChatBskyConvoDefs.ConvoView | undefined
   sender: AppBskyActorDefs.ProfileViewBasic | undefined
@@ -587,7 +593,7 @@ export class Convo {
       logger.error('Convo: failed to fetch message history')
 
       this.headerItems.set(ConvoItemError.HistoryFailed, {
-        type: 'error-recoverable',
+        type: 'error',
         key: ConvoItemError.HistoryFailed,
         code: ConvoItemError.HistoryFailed,
         retry: () => {
@@ -635,7 +641,7 @@ export class Convo {
 
   onFirehoseError(error?: MessagesEventBusError) {
     this.footerItems.set(ConvoItemError.FirehoseFailed, {
-      type: 'error-recoverable',
+      type: 'error',
       key: ConvoItemError.FirehoseFailed,
       code: ConvoItemError.FirehoseFailed,
       retry: () => {
@@ -724,7 +730,7 @@ export class Convo {
     }
   }
 
-  private pendingFailed = false
+  private pendingMessageFailure: 'recoverable' | 'unrecoverable' | null = null
 
   async sendMessage(message: ChatBskyConvoSendMessage.InputSchema['message']) {
     // Ignore empty messages for now since they have no other purpose atm
@@ -740,7 +746,7 @@ export class Convo {
     })
     this.commit()
 
-    if (!this.isProcessingPendingMessages && !this.pendingFailed) {
+    if (!this.isProcessingPendingMessages && !this.pendingMessageFailure) {
       this.processPendingMessages()
     }
   }
@@ -765,7 +771,6 @@ export class Convo {
     try {
       this.isProcessingPendingMessages = true
 
-      // throw new Error('UNCOMMENT TO TEST RETRY')
       const {id, message} = pendingMessage
 
       const response = await networkRetry(2, () => {
@@ -794,13 +799,47 @@ export class Convo {
       this.commit()
     } catch (e: any) {
       logger.error(e, {context: `Convo: failed to send message`})
-      this.pendingFailed = true
-      this.commit()
+      this.handleSendMessageFailure(e)
     } finally {
       this.isProcessingPendingMessages = false
     }
   }
 
+  private handleSendMessageFailure(e: any) {
+    if (e instanceof XRPCError) {
+      if (NETWORK_FAILURE_STATUSES.includes(e.status)) {
+        this.pendingMessageFailure = 'recoverable'
+      } else {
+        switch (e.message) {
+          case 'block between recipient and sender':
+            this.pendingMessageFailure = 'unrecoverable'
+            this.emitter.emit('event', {type: 'sync-convo-state'})
+            break
+          default:
+            logger.warn(
+              `Convo handleSendMessageFailure could not handle error`,
+              {
+                status: e.status,
+                message: e.message,
+              },
+            )
+            break
+        }
+      }
+    } else {
+      logger.warn(`Convo handleSendMessageFailure received unknown error`, {
+        message: e.message,
+      })
+      this.footerItems.set(ConvoItemError.Unknown, {
+        type: 'error',
+        key: ConvoItemError.Unknown,
+        code: ConvoItemError.Unknown,
+      })
+    }
+
+    this.commit()
+  }
+
   async batchRetryPendingMessages() {
     logger.debug(
       `Convo: retrying ${this.pendingMessages.size} pending messages`,
@@ -848,8 +887,7 @@ export class Convo {
       )
     } catch (e: any) {
       logger.error(e, {context: `Convo: failed to batch retry messages`})
-      this.pendingFailed = true
-      this.commit()
+      this.handleSendMessageFailure(e)
     }
   }
 
@@ -877,6 +915,14 @@ export class Convo {
     }
   }
 
+  on(handler: (event: ConvoEvent) => void) {
+    this.emitter.on('event', handler)
+
+    return () => {
+      this.emitter.off('event', handler)
+    }
+  }
+
   /*
    * Items in reverse order, since FlatList inverts
    */
@@ -940,13 +986,15 @@ export class Convo {
           sender: this.sender!,
         },
         nextMessage: null,
-        retry: this.pendingFailed
-          ? () => {
-              this.pendingFailed = false
-              this.commit()
-              this.batchRetryPendingMessages()
-            }
-          : undefined,
+        failed: this.pendingMessageFailure !== null,
+        retry:
+          this.pendingMessageFailure === 'recoverable'
+            ? () => {
+                this.pendingMessageFailure = null
+                this.commit()
+                this.batchRetryPendingMessages()
+              }
+            : undefined,
       })
     })
 
diff --git a/src/state/messages/convo/const.ts b/src/state/messages/convo/const.ts
index abea5205eb..6ce100d11e 100644
--- a/src/state/messages/convo/const.ts
+++ b/src/state/messages/convo/const.ts
@@ -1,3 +1,7 @@
 export const ACTIVE_POLL_INTERVAL = 1e3
 export const BACKGROUND_POLL_INTERVAL = 5e3
 export const INACTIVE_TIMEOUT = 60e3 * 5
+
+export const NETWORK_FAILURE_STATUSES = [
+  1, 408, 425, 429, 500, 502, 503, 504, 522, 524,
+]
diff --git a/src/state/messages/convo/index.tsx b/src/state/messages/convo/index.tsx
index e955d41183..1e8cef2e88 100644
--- a/src/state/messages/convo/index.tsx
+++ b/src/state/messages/convo/index.tsx
@@ -78,6 +78,16 @@ export function ConvoProvider({
     }, [convo, convoId, markAsRead]),
   )
 
+  React.useEffect(() => {
+    return convo.on(event => {
+      switch (event.type) {
+        case 'sync-convo-state': {
+          console.log('SYNC')
+        }
+      }
+    })
+  }, [convo])
+
   React.useEffect(() => {
     const handleAppStateChange = (nextAppState: string) => {
       if (isScreenFocused) {
diff --git a/src/state/messages/convo/types.ts b/src/state/messages/convo/types.ts
index 3fb0eb6ad3..d7490acbe6 100644
--- a/src/state/messages/convo/types.ts
+++ b/src/state/messages/convo/types.ts
@@ -26,7 +26,7 @@ export enum ConvoItemError {
   /**
    * Generic error
    */
-  Network = 'network',
+  Unknown = 'unknown',
   /**
    * Error connecting to event firehose
    */
@@ -35,6 +35,10 @@ export enum ConvoItemError {
    * Error fetching past messages
    */
   HistoryFailed = 'historyFailed',
+  /**
+   * Recipient is blocking the user
+   */
+  UserBlocked = 'userBlocked',
 }
 
 export enum ConvoErrorCode {
@@ -95,6 +99,7 @@ export type ConvoItem =
         | ChatBskyConvoDefs.MessageView
         | ChatBskyConvoDefs.DeletedMessageView
         | null
+      failed: boolean
       /**
        * Retry sending the message. If present, the message is in a failed state.
        */
@@ -110,10 +115,13 @@ export type ConvoItem =
         | null
     }
   | {
-      type: 'error-recoverable'
+      type: 'error'
       key: string
       code: ConvoItemError
-      retry: () => void
+      /**
+       * If present, error is recoverable.
+       */
+      retry?: () => void
     }
 
 type DeleteMessage = (messageId: string) => Promise<void>
@@ -201,3 +209,7 @@ export type ConvoState =
   | ConvoStateBackgrounded
   | ConvoStateSuspended
   | ConvoStateError
+
+export type ConvoEvent = {
+  type: 'sync-convo-state'
+}