diff --git a/ts/signal.ts b/ts/signal.ts
index e1f5890854..857f64ffdb 100644
--- a/ts/signal.ts
+++ b/ts/signal.ts
@@ -247,6 +247,7 @@ export function initializeMigrations({
         getImageDimensions,
         makeImageThumbnail,
         makeVideoScreenshot,
+        deleteOnDisk,
         logger,
       }),
     processNewSticker: (stickerData: Uint8Array) =>
@@ -282,6 +283,7 @@ export function initializeMigrations({
         maxVersion,
         getAbsoluteStickerPath,
         writeNewStickerData,
+        deleteOnDisk,
       });
     },
     writeMessageAttachments: MessageType.createAttachmentDataWriter({
diff --git a/ts/test-node/types/Message2_test.ts b/ts/test-node/types/Message2_test.ts
index 36d524e1fb..17d740a4dc 100644
--- a/ts/test-node/types/Message2_test.ts
+++ b/ts/test-node/types/Message2_test.ts
@@ -73,6 +73,7 @@ describe('Message', () => {
       writeNewAttachmentData: async (_data: Uint8Array) =>
         'fake-attachment-path',
       writeNewStickerData: async (_data: Uint8Array) => 'fake-sticker-path',
+      deleteOnDisk: async (_path: string) => undefined,
       ...props,
     };
   }
diff --git a/ts/types/Message2.ts b/ts/types/Message2.ts
index e1e5ffac59..6e8c3987f2 100644
--- a/ts/types/Message2.ts
+++ b/ts/types/Message2.ts
@@ -72,6 +72,7 @@ export type ContextType = {
   revokeObjectUrl: (objectUrl: string) => void;
   writeNewAttachmentData: (data: Uint8Array) => Promise<string>;
   writeNewStickerData: (data: Uint8Array) => Promise<string>;
+  deleteOnDisk: (path: string) => Promise<void>;
 };
 
 type WriteExistingAttachmentDataType = (
@@ -373,7 +374,26 @@ const toVersion0 = async (
 ) => initializeSchemaVersion({ message, logger: context.logger });
 const toVersion1 = _withSchemaVersion({
   schemaVersion: 1,
-  upgrade: _mapAttachments(autoOrientJPEG),
+  upgrade: _mapAttachments(
+    async (
+      attachment: AttachmentType,
+      context,
+      options
+    ): Promise<AttachmentType> => {
+      const { deleteOnDisk } = context;
+      const rotatedAttachment = await autoOrientJPEG(
+        attachment,
+        context,
+        options
+      );
+
+      if (attachment.path) {
+        await deleteOnDisk(attachment.path);
+      }
+
+      return rotatedAttachment;
+    }
+  ),
 });
 const toVersion2 = _withSchemaVersion({
   schemaVersion: 2,
@@ -479,6 +499,7 @@ export const upgradeSchema = async (
     makeImageThumbnail,
     makeVideoScreenshot,
     writeNewStickerData,
+    deleteOnDisk,
     logger,
     maxVersion = CURRENT_SCHEMA_VERSION,
   }: ContextType
@@ -516,6 +537,9 @@ export const upgradeSchema = async (
   if (!isFunction(writeNewStickerData)) {
     throw new TypeError('context.writeNewStickerData is required');
   }
+  if (!isFunction(deleteOnDisk)) {
+    throw new TypeError('context.deleteOnDisk is required');
+  }
 
   let message = rawMessage;
   for (let index = 0, max = VERSIONS.length; index < max; index += 1) {
@@ -539,6 +563,7 @@ export const upgradeSchema = async (
       getAbsoluteStickerPath,
       getRegionCode,
       writeNewStickerData,
+      deleteOnDisk,
     });
   }
 
@@ -557,6 +582,7 @@ export const processNewAttachment = async (
     getImageDimensions,
     makeImageThumbnail,
     makeVideoScreenshot,
+    deleteOnDisk,
     logger,
   }: Pick<
     ContextType,
@@ -568,6 +594,7 @@ export const processNewAttachment = async (
     | 'makeImageThumbnail'
     | 'makeVideoScreenshot'
     | 'logger'
+    | 'deleteOnDisk'
   >
 ): Promise<AttachmentType> => {
   if (!isFunction(writeNewAttachmentData)) {
@@ -612,6 +639,10 @@ export const processNewAttachment = async (
       writeNewAttachmentData,
       logger,
     });
+
+    if (attachment.path) {
+      await deleteOnDisk(attachment.path);
+    }
   }
 
   const finalAttachment = await captureDimensionsAndScreenshot(
diff --git a/ts/util/attachments.ts b/ts/util/attachments.ts
index 89484d5f97..0775cc8288 100644
--- a/ts/util/attachments.ts
+++ b/ts/util/attachments.ts
@@ -78,10 +78,14 @@ export async function autoOrientJPEG(
     // retain it but due to reports of data loss, we don’t want to overburden IndexedDB
     // by potentially doubling stored image data.
     // See: https://github.com/signalapp/Signal-Desktop/issues/1589
+    // We also clear out the attachment path because we're changing
+    // the attachment data so it no longer matches the old path.
+    // Path and data should always be in agreement.
     const xcodedAttachment = {
       ...attachment,
       data: new Uint8Array(xcodedDataArrayBuffer),
       size: xcodedDataArrayBuffer.byteLength,
+      path: undefined,
     };
 
     return xcodedAttachment;