diff --git a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentDatabase.java b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentDatabase.java
index 80443293ab..45fbb57d93 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentDatabase.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/database/AttachmentDatabase.java
@@ -535,14 +535,10 @@ public class AttachmentDatabase extends Database {
     }
 
     values.put(TRANSFER_STATE, TRANSFER_PROGRESS_DONE);
-    values.put(CDN_NUMBER, 0);
-    values.put(CONTENT_LOCATION, (String)null);
-    values.put(CONTENT_DISPOSITION, (String)null);
-    values.put(DIGEST, (byte[])null);
-    values.put(NAME, (String) null);
-    values.put(FAST_PREFLIGHT_ID, (String)null);
     values.put(TRANSFER_FILE, (String)null);
 
+    values.put(TRANSFORM_PROPERTIES, TransformProperties.forSkipTransform().serialize());
+
     if (database.update(TABLE_NAME, values, PART_ID_WHERE, attachmentId.toStrings()) == 0) {
       //noinspection ResultOfMethodCallIgnored
       dataInfo.file.delete();
@@ -1198,7 +1194,9 @@ public class AttachmentDatabase extends Database {
       }
     }
 
-    boolean useTemplateUpload = template.getUploadTimestamp() > attachment.getUploadTimestamp() && template.getTransferState() == TRANSFER_PROGRESS_DONE;
+    boolean useTemplateUpload = template.getUploadTimestamp() > attachment.getUploadTimestamp() &&
+                                template.getTransferState() == TRANSFER_PROGRESS_DONE           &&
+                                template.getTransformProperties().shouldSkipTransform();
 
     ContentValues contentValues = new ContentValues();
     contentValues.put(MMS_ID, mmsId);
diff --git a/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java b/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java
index 1e08a9117b..dd0cc8b686 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java
+++ b/app/src/main/java/org/thoughtcrime/securesms/jobs/AttachmentUploadJob.java
@@ -4,6 +4,7 @@ import android.graphics.Bitmap;
 import android.media.MediaDataSource;
 import android.media.MediaMetadataRetriever;
 import android.os.Build;
+import android.text.TextUtils;
 
 import androidx.annotation.NonNull;
 import androidx.annotation.Nullable;
@@ -114,7 +115,7 @@ public final class AttachmentUploadJob extends BaseJob {
     }
 
     long timeSinceUpload = System.currentTimeMillis() - databaseAttachment.getUploadTimestamp();
-    if (timeSinceUpload < UPLOAD_REUSE_THRESHOLD) {
+    if (timeSinceUpload < UPLOAD_REUSE_THRESHOLD && !TextUtils.isEmpty(databaseAttachment.getLocation())) {
       Log.i(TAG, "We can re-use an already-uploaded file. It was uploaded " + timeSinceUpload + " ms ago. Skipping.");
       return;
     } else if (databaseAttachment.getUploadTimestamp() > 0) {