diff --git a/ts/sql/Interface.ts b/ts/sql/Interface.ts
index 1c77bcf214a..16595b342a5 100644
--- a/ts/sql/Interface.ts
+++ b/ts/sql/Interface.ts
@@ -1238,6 +1238,8 @@ type WritableInterface = {
 
   processGroupCallRingCancellation(ringId: bigint): void;
   cleanExpiredGroupCallRingCancellations(): void;
+
+  _testOnlyRemoveMessageAttachments(timestamp: number): void;
 };
 
 // Adds a database argument
diff --git a/ts/sql/Server.ts b/ts/sql/Server.ts
index 253fd24dd7c..628c35482b4 100644
--- a/ts/sql/Server.ts
+++ b/ts/sql/Server.ts
@@ -705,6 +705,8 @@ export const DataWriter: ServerWritableInterface = {
   disableFSync,
   enableFSyncAndCheckpoint,
 
+  _testOnlyRemoveMessageAttachments,
+
   // Server-only
 
   removeKnownStickers,
@@ -2720,6 +2722,17 @@ function saveMessageAttachment({
   ).run(values);
 }
 
+function _testOnlyRemoveMessageAttachments(
+  db: WritableDB,
+  timestamp: number
+): void {
+  const [query, params] = sql`
+    DELETE FROM message_attachments
+      WHERE sentAt = ${timestamp};`;
+
+  db.prepare(query).run(params);
+}
+
 function saveMessage(
   db: WritableDB,
   message: ReadonlyDeep<MessageType>,
diff --git a/ts/sql/hydration.ts b/ts/sql/hydration.ts
index 357cf6caec1..a0adb6cc9ce 100644
--- a/ts/sql/hydration.ts
+++ b/ts/sql/hydration.ts
@@ -23,13 +23,20 @@ import {
   sql,
   sqlJoin,
 } from './util';
-import type { AttachmentType } from '../types/Attachment';
-import { IMAGE_JPEG, stringToMIMEType } from '../types/MIME';
+import { type AttachmentType } from '../types/Attachment';
+import {
+  APPLICATION_OCTET_STREAM,
+  IMAGE_JPEG,
+  IMAGE_PNG,
+  stringToMIMEType,
+} from '../types/MIME';
 import { strictAssert } from '../util/assert';
 import type { MessageAttributesType } from '../model-types';
+import { createLogger } from '../logging/log';
 
 export const ROOT_MESSAGE_ATTACHMENT_EDIT_HISTORY_INDEX = -1;
 
+const log = createLogger('hydrateMessage');
 function toBoolean(value: number | null): boolean | undefined {
   if (value == null) {
     return undefined;
@@ -48,9 +55,12 @@ export function hydrateMessages(
   db: ReadableDB,
   unhydratedMessages: Array<MessageTypeUnhydrated>
 ): Array<MessageType> {
-  const messagesWithColumnsHydrated = unhydratedMessages.map(
-    hydrateMessageTableColumns
-  );
+  const messagesWithColumnsHydrated = unhydratedMessages.map(msg => ({
+    ...hydrateMessageTableColumns(msg),
+    hasAttachments: msg.hasAttachments === 1,
+    hasFileAttachments: msg.hasFileAttachments === 1,
+    hasVisualMediaAttachments: msg.hasVisualMediaAttachments === 1,
+  }));
 
   return hydrateMessagesWithAttachments(db, messagesWithColumnsHydrated);
 }
@@ -142,7 +152,13 @@ export function getAttachmentReferencesForMessages(
 
 function hydrateMessagesWithAttachments(
   db: ReadableDB,
-  messagesWithoutAttachments: Array<MessageType>
+  messagesWithoutAttachments: Array<
+    MessageType & {
+      hasAttachments: boolean;
+      hasVisualMediaAttachments: boolean;
+      hasFileAttachments: boolean;
+    }
+  >
 ): Array<MessageType> {
   const attachmentReferencesForAllMessages = getAttachmentReferencesForMessages(
     db,
@@ -153,10 +169,56 @@ function hydrateMessagesWithAttachments(
     'messageId'
   );
 
-  return messagesWithoutAttachments.map(msg => {
+  return messagesWithoutAttachments.map(msgWithExtraFields => {
+    const {
+      hasAttachments,
+      hasFileAttachments,
+      hasVisualMediaAttachments,
+      ...msg
+    } = msgWithExtraFields;
+
     const attachmentReferences = attachmentReferencesByMessage[msg.id] ?? [];
+
     if (!attachmentReferences.length) {
-      return msg;
+      if (msg.attachments?.length) {
+        // legacy message, attachments still on JSON
+        return msg;
+      }
+
+      if (msg.isErased || msg.deletedForEveryone || msg.isViewOnce) {
+        return msg;
+      }
+
+      if (msg.type !== 'incoming' && msg.type !== 'outgoing') {
+        return msg;
+      }
+
+      if (
+        !hasAttachments &&
+        !hasFileAttachments &&
+        !hasVisualMediaAttachments
+      ) {
+        return msg;
+      }
+
+      log.warn(
+        `Retrieved message that should have attachments but missing message_attachment rows, timestamp: ${msg.timestamp}`
+      );
+      // Add an empty attachment to the message to enable backfilling in the UI
+      return {
+        ...msg,
+        attachments: [
+          {
+            error: true,
+            size: 0,
+            width: hasVisualMediaAttachments ? 150 : undefined,
+            height: hasVisualMediaAttachments ? 150 : undefined,
+            contentType: hasVisualMediaAttachments
+              ? IMAGE_PNG
+              : APPLICATION_OCTET_STREAM,
+          },
+        ],
+      };
     }
 
     const attachmentsByEditHistoryIndex = groupBy(
diff --git a/ts/test-electron/normalizedAttachments_test.ts b/ts/test-electron/normalizedAttachments_test.ts
index 5eddcf06761..50ea1446826 100644
--- a/ts/test-electron/normalizedAttachments_test.ts
+++ b/ts/test-electron/normalizedAttachments_test.ts
@@ -688,4 +688,28 @@ describe('normalizes attachment references', () => {
       omit(attachmentWithoutKey, 'randomKey')
     );
   });
+
+  it('adds a placeholder attachment when attachments had been deleted', async () => {
+    const message = composeMessage(Date.now(), {
+      attachments: [composeAttachment(), composeAttachment()],
+    });
+
+    await DataWriter.saveMessage(message, {
+      forceSave: true,
+      ourAci: generateAci(),
+      postSaveUpdates: () => Promise.resolve(),
+    });
+
+    await DataWriter._testOnlyRemoveMessageAttachments(message.timestamp);
+
+    const messageFromDB = await DataReader.getMessageById(message.id);
+    assert(messageFromDB, 'message was saved');
+    assert.deepEqual(messageFromDB.attachments?.[0], {
+      size: 0,
+      contentType: IMAGE_PNG,
+      width: 150,
+      height: 150,
+      error: true,
+    });
+  });
 });