diff --git a/ts/messageModifiers/AttachmentDownloads.ts b/ts/messageModifiers/AttachmentDownloads.ts
index f08e7af40e..1fffa349ea 100644
--- a/ts/messageModifiers/AttachmentDownloads.ts
+++ b/ts/messageModifiers/AttachmentDownloads.ts
@@ -221,6 +221,7 @@ async function _maybeStartJob(): Promise<void> {
         const logId = `attachment_downloads/_maybeStartJob/postProcess/${job.id}`;
         try {
           await promise;
+          log.info(`${logId}: job has finished running`);
           if (_activeAttachmentDownloadJobs[job.id]) {
             throw new Error(
               `${logId}: Active attachments jobs list still has this job!`
@@ -341,6 +342,10 @@ async function _runJob(job?: AttachmentDownloadJobType): Promise<void> {
       return;
     }
 
+    logger.info(
+      `attachment_downloads/_runJob(${id}): processing new attachment` +
+        ` of type: ${type}`
+    );
     const upgradedAttachment =
       await window.Signal.Migrations.processNewAttachment(downloaded);
 
@@ -470,6 +475,10 @@ async function _finishJob(
     await saveMessage(message.attributes, {
       ourAci: window.textsecure.storage.user.getCheckedAci(),
     });
+  } else {
+    logger.info(
+      `attachment_downloads/_finishJob for job id: ${id} without message`
+    );
   }
 
   await removeAttachmentDownloadJob(id);
@@ -516,6 +525,8 @@ async function _addAttachmentToMessage(
   const logPrefix = `${message.idForLogging()} (type: ${type}, index: ${index})`;
   const attachmentSignature = getAttachmentSignature(attachment);
 
+  log.info(`${logPrefix}: _addAttachmentToMessage: starting`);
+
   if (type === 'long-message') {
     let handledAnywhere = false;
     let attachmentData: Uint8Array | undefined;
@@ -601,6 +612,7 @@ async function _addAttachmentToMessage(
           `${logPrefix}: Long message attachment found no matching place to apply`
         );
       }
+      log.info(`${logPrefix}: _addAttachmentToMessage finished`);
     }
     return;
   }
diff --git a/ts/textsecure/downloadAttachment.ts b/ts/textsecure/downloadAttachment.ts
index 91ed0590e1..e97230b892 100644
--- a/ts/textsecure/downloadAttachment.ts
+++ b/ts/textsecure/downloadAttachment.ts
@@ -100,8 +100,11 @@ export async function downloadAttachmentV2(
     dropNull(cdnNumber),
     options
   );
+  log.info(`${logId} got download stream`);
 
   const cipherTextRelativePath = await downloadToDisk({ downloadStream, size });
+  log.info(`${logId} downloaded encrypted file to disk`);
+
   const cipherTextAbsolutePath =
     window.Signal.Migrations.getAbsoluteAttachmentPath(cipherTextRelativePath);
 
@@ -112,6 +115,7 @@ export async function downloadAttachmentV2(
     size,
     theirDigest: Bytes.fromBase64(digest),
   });
+  log.info(`${logId} successfully decrypted`);
 
   safeUnlinkSync(cipherTextAbsolutePath);
 
diff --git a/ts/types/Attachment.ts b/ts/types/Attachment.ts
index 6e3891d9b6..6b5e469738 100644
--- a/ts/types/Attachment.ts
+++ b/ts/types/Attachment.ts
@@ -413,15 +413,19 @@ export async function captureDimensionsAndScreenshot(
   if (!attachment.path) {
     return attachment;
   }
+  logger.info('captureDimensionsAndScreenshot: starting');
 
   const absolutePath = getAbsoluteAttachmentPath(attachment.path);
 
   if (GoogleChrome.isImageTypeSupported(contentType)) {
     try {
+      logger.info('captureDimensionsAndScreenshot: getting image dimensions');
       const { width, height } = await getImageDimensionsFromURL({
         objectUrl: absolutePath,
         logger,
       });
+
+      logger.info('captureDimensionsAndScreenshot: generating thumbnail');
       const thumbnailBuffer = await blobToArrayBuffer(
         await makeImageThumbnail({
           size: THUMBNAIL_SIZE,
@@ -430,7 +434,7 @@ export async function captureDimensionsAndScreenshot(
           logger,
         })
       );
-
+      logger.info('captureDimensionsAndScreenshot: writing thumbnail');
       const thumbnailPath = await writeNewAttachmentData(
         new Uint8Array(thumbnailBuffer)
       );
@@ -457,6 +461,7 @@ export async function captureDimensionsAndScreenshot(
 
   let screenshotObjectUrl: string | undefined;
   try {
+    logger.info('captureDimensionsAndScreenshot: making video screenshot');
     const screenshotBuffer = await blobToArrayBuffer(
       await makeVideoScreenshot({
         objectUrl: absolutePath,
@@ -468,14 +473,17 @@ export async function captureDimensionsAndScreenshot(
       screenshotBuffer,
       THUMBNAIL_CONTENT_TYPE
     );
+    logger.info('captureDimensionsAndScreenshot: getting image dimensions');
     const { width, height } = await getImageDimensionsFromURL({
       objectUrl: screenshotObjectUrl,
       logger,
     });
+    logger.info('captureDimensionsAndScreenshot: writing attachment data');
     const screenshotPath = await writeNewAttachmentData(
       new Uint8Array(screenshotBuffer)
     );
 
+    logger.info('captureDimensionsAndScreenshot: making thumbnail');
     const thumbnailBuffer = await blobToArrayBuffer(
       await makeImageThumbnail({
         size: THUMBNAIL_SIZE,
@@ -485,6 +493,7 @@ export async function captureDimensionsAndScreenshot(
       })
     );
 
+    logger.info('captureDimensionsAndScreenshot: writing thumbnail');
     const thumbnailPath = await writeNewAttachmentData(
       new Uint8Array(thumbnailBuffer)
     );