diff --git a/ts/types/Message2.ts b/ts/types/Message2.ts
index 3105400085..9616eceffe 100644
--- a/ts/types/Message2.ts
+++ b/ts/types/Message2.ts
@@ -466,21 +466,26 @@ const toVersion12 = _withSchemaVersion({
 
     const result = { ...message };
 
+    const logId = `Message2.toVersion12(${message.sent_at})`;
+
     if (attachments?.length) {
       result.attachments = await Promise.all(
-        attachments.map(async attachment => {
-          const copy = await encryptLegacyAttachment(attachment, context);
+        attachments.map(async (attachment, i) => {
+          const copy = await encryptLegacyAttachment(attachment, {
+            ...context,
+            logId: `${logId}.attachments[${i}]`,
+          });
           if (copy.thumbnail) {
-            copy.thumbnail = await encryptLegacyAttachment(
-              copy.thumbnail,
-              context
-            );
+            copy.thumbnail = await encryptLegacyAttachment(copy.thumbnail, {
+              ...context,
+              logId: `${logId}.attachments[${i}].thumbnail`,
+            });
           }
           if (copy.screenshot) {
-            copy.screenshot = await encryptLegacyAttachment(
-              copy.screenshot,
-              context
-            );
+            copy.screenshot = await encryptLegacyAttachment(copy.screenshot, {
+              ...context,
+              logId: `${logId}.attachments[${i}].screenshot`,
+            });
           }
           return copy;
         })
@@ -488,31 +493,27 @@ const toVersion12 = _withSchemaVersion({
     }
 
     if (quote && quote.attachments?.length) {
-      try {
-        result.quote = {
-          ...quote,
-          attachments: await Promise.all(
-            quote.attachments.map(async quoteAttachment => {
-              return {
-                ...quoteAttachment,
-                thumbnail:
-                  quoteAttachment.thumbnail &&
-                  (await encryptLegacyAttachment(
-                    quoteAttachment.thumbnail,
-                    context
-                  )),
-              };
-            })
-          ),
-        };
-      } catch (error) {
-        context.logger.error(`Failed to migrate quote for ${message.id}`);
-      }
+      result.quote = {
+        ...quote,
+        attachments: await Promise.all(
+          quote.attachments.map(async (quoteAttachment, i) => {
+            return {
+              ...quoteAttachment,
+              thumbnail:
+                quoteAttachment.thumbnail &&
+                (await encryptLegacyAttachment(quoteAttachment.thumbnail, {
+                  ...context,
+                  logId: `${logId}.quote[${i}].thumbnail`,
+                })),
+            };
+          })
+        ),
+      };
     }
 
     if (contact?.length) {
       result.contact = await Promise.all(
-        contact.map(async c => {
+        contact.map(async (c, i) => {
           if (!c.avatar?.avatar) {
             return c;
           }
@@ -521,7 +522,10 @@ const toVersion12 = _withSchemaVersion({
             ...c,
             avatar: {
               ...c.avatar,
-              avatar: await encryptLegacyAttachment(c.avatar.avatar, context),
+              avatar: await encryptLegacyAttachment(c.avatar.avatar, {
+                ...context,
+                logId: `${logId}.contact[${i}].avatar`,
+              }),
             },
           };
         })
@@ -530,14 +534,17 @@ const toVersion12 = _withSchemaVersion({
 
     if (preview?.length) {
       result.preview = await Promise.all(
-        preview.map(async p => {
+        preview.map(async (p, i) => {
           if (!p.image) {
             return p;
           }
 
           return {
             ...p,
-            image: await encryptLegacyAttachment(p.image, context),
+            image: await encryptLegacyAttachment(p.image, {
+              ...context,
+              logId: `${logId}.preview[${i}].image`,
+            }),
           };
         })
       );
@@ -547,10 +554,16 @@ const toVersion12 = _withSchemaVersion({
       result.sticker = {
         ...sticker,
         data: sticker.data && {
-          ...(await encryptLegacyAttachment(sticker.data, context)),
+          ...(await encryptLegacyAttachment(sticker.data, {
+            ...context,
+            logId: `${logId}.sticker.data`,
+          })),
           thumbnail:
             sticker.data.thumbnail &&
-            (await encryptLegacyAttachment(sticker.data.thumbnail, context)),
+            (await encryptLegacyAttachment(sticker.data.thumbnail, {
+              ...context,
+              logId: `${logId}.sticker.thumbnail`,
+            })),
         },
       };
     }
diff --git a/ts/types/Stickers.ts b/ts/types/Stickers.ts
index 8a01bf273e..8599e2c425 100644
--- a/ts/types/Stickers.ts
+++ b/ts/types/Stickers.ts
@@ -1009,6 +1009,7 @@ async function encryptLegacySticker(
     window.Signal.Migrations;
 
   const updated = await encryptLegacyAttachment(sticker, {
+    logId: 'sticker',
     readAttachmentData: readStickerData,
     writeNewAttachmentData: writeNewStickerData,
     disposition: AttachmentDisposition.Sticker,
diff --git a/ts/util/encryptConversationAttachments.ts b/ts/util/encryptConversationAttachments.ts
index 46cfc5a211..c48c7b7d14 100644
--- a/ts/util/encryptConversationAttachments.ts
+++ b/ts/util/encryptConversationAttachments.ts
@@ -10,6 +10,7 @@ import { encryptLegacyAttachment } from './encryptLegacyAttachment';
 import { AttachmentDisposition } from './getLocalAttachmentUrl';
 import { isNotNil } from './isNotNil';
 import { isSignalConversation } from './isSignalConversation';
+import { getConversationIdForLogging } from './idForLogging';
 
 const CONCURRENCY = 32;
 
@@ -66,6 +67,7 @@ async function encryptOne(attributes: ConversationAttributesType): Promise<
     return undefined;
   }
 
+  const logId = getConversationIdForLogging(attributes);
   const result = { ...attributes };
 
   const {
@@ -86,6 +88,7 @@ async function encryptOne(attributes: ConversationAttributesType): Promise<
     result.profileAvatar = await encryptLegacyAttachment(
       attributes.profileAvatar,
       {
+        logId: `${logId}.profileAvatar`,
         readAttachmentData,
         writeNewAttachmentData,
         disposition: AttachmentDisposition.Attachment,
@@ -99,6 +102,7 @@ async function encryptOne(attributes: ConversationAttributesType): Promise<
 
   if (attributes.avatar?.path) {
     result.avatar = await encryptLegacyAttachment(attributes.avatar, {
+      logId: `${logId}.avatar`,
       readAttachmentData,
       writeNewAttachmentData,
       disposition: AttachmentDisposition.Attachment,
@@ -111,7 +115,7 @@ async function encryptOne(attributes: ConversationAttributesType): Promise<
 
   if (attributes.avatars?.length) {
     result.avatars = await Promise.all(
-      attributes.avatars.map(async avatar => {
+      attributes.avatars.map(async (avatar, i) => {
         if (avatar.version === 2 || !avatar.imagePath) {
           return avatar;
         }
@@ -121,6 +125,7 @@ async function encryptOne(attributes: ConversationAttributesType): Promise<
             path: avatar.imagePath,
           },
           {
+            logId: `${logId}.avatars[${i}]`,
             readAttachmentData: readAvatarData,
             writeNewAttachmentData: writeNewAvatarData,
             disposition: AttachmentDisposition.AvatarData,
@@ -141,8 +146,9 @@ async function encryptOne(attributes: ConversationAttributesType): Promise<
 
   if (attributes.draftAttachments?.length) {
     result.draftAttachments = await Promise.all(
-      attributes.draftAttachments.map(async draft => {
+      attributes.draftAttachments.map(async (draft, i) => {
         const updated = await encryptLegacyAttachment(draft, {
+          logId: `${logId}.draft[${i}]`,
           readAttachmentData: readDraftData,
           writeNewAttachmentData: writeNewDraftData,
           disposition: AttachmentDisposition.Draft,
diff --git a/ts/util/encryptLegacyAttachment.ts b/ts/util/encryptLegacyAttachment.ts
index 7231704396..8b3e6fe7c0 100644
--- a/ts/util/encryptLegacyAttachment.ts
+++ b/ts/util/encryptLegacyAttachment.ts
@@ -2,10 +2,12 @@
 // SPDX-License-Identifier: AGPL-3.0-only
 
 import LRU from 'lru-cache';
+
 import type {
   AddressableAttachmentType,
   LocalAttachmentV2Type,
 } from '../types/Attachment';
+import * as log from '../logging/log';
 import { AttachmentDisposition } from './getLocalAttachmentUrl';
 
 let setCheck = false;
@@ -15,6 +17,7 @@ const lru = new LRU<string, Promise<LocalAttachmentV2Type>>({
 });
 
 export type EncryptLegacyAttachmentOptionsType = Readonly<{
+  logId: string;
   disposition?: AttachmentDisposition;
   readAttachmentData: (
     attachment: Partial<AddressableAttachmentType>
@@ -43,12 +46,18 @@ export async function encryptLegacyAttachment<
     promise = doEncrypt(attachment, options);
     lru.set(cacheKey, promise);
   }
-  const modern = await promise;
+  try {
+    const modern = await promise;
 
-  return {
-    ...attachment,
-    ...modern,
-  };
+    return {
+      ...attachment,
+      ...modern,
+    };
+  } catch (error) {
+    const { logId } = options;
+    log.error(`${logId}: migration failed, falling back to original`, error);
+    return attachment;
+  }
 }
 
 async function doEncrypt<T extends Partial<AddressableAttachmentType>>(