diff --git a/stylesheets/_modules.scss b/stylesheets/_modules.scss
index f5a3525a0..cff75a61b 100644
--- a/stylesheets/_modules.scss
+++ b/stylesheets/_modules.scss
@@ -11542,9 +11542,6 @@ $contact-modal-padding: 18px;
 
 // To limit messages with things forcing them wider, like long attachment names
 .module-message__container {
-  // 2px to allow for 1px border
-  max-width: 302px;
-
   &--incoming {
     align-self: flex-start;
   }
@@ -11679,15 +11676,20 @@ $contact-modal-padding: 18px;
   }
 }
 
+/* Spec: container < 437px */
+@media (min-width: 0px) and (max-width: 799px) {
+  .module-message {
+    // Add 2px for 1px border
+    max-width: 302px;
+  }
+}
+
 /* Spec: container > 438px and container < 593px */
 @media (min-width: 800px) and (max-width: 925px) {
   .module-message {
     // Add 2px for 1px border
     max-width: 376px;
   }
-  .module-message__container {
-    max-width: 100%;
-  }
 
   // Spec: container < 438px
   .module-message--incoming {
@@ -11722,9 +11724,6 @@ $contact-modal-padding: 18px;
   .module-message {
     max-width: 66%;
   }
-  .module-message__container {
-    max-width: 100%;
-  }
 
   .module-message--incoming {
     margin-right: auto;
diff --git a/ts/background.ts b/ts/background.ts
index 2c6b22cca..c02714d3a 100644
--- a/ts/background.ts
+++ b/ts/background.ts
@@ -626,7 +626,17 @@ type WhatIsThis = import('./window.d').WhatIsThis;
     Views.Initialization.setMessage(window.i18n('optimizingApplication'));
 
     if (newVersion) {
-      await window.Signal.Data.cleanupOrphanedAttachments();
+      // We've received reports that this update can take longer than two minutes, so we
+      //   allow it to continue and just move on in that timeout case.
+      try {
+        await window.Signal.Data.cleanupOrphanedAttachments();
+      } catch (error) {
+        window.log.error(
+          'background: Failed to cleanup orphaned attachments:',
+          error && error.stack ? error.stack : error
+        );
+      }
+
       // Don't block on the following operation
       window.Signal.Data.ensureFilePermissions();
     }
diff --git a/ts/components/conversation/Message.stories.tsx b/ts/components/conversation/Message.stories.tsx
index c9afc3b52..39e838b6d 100644
--- a/ts/components/conversation/Message.stories.tsx
+++ b/ts/components/conversation/Message.stories.tsx
@@ -755,6 +755,23 @@ story.add('Other File Type with Caption', () => {
   return renderBothDirections(props);
 });
 
+story.add('Other File Type with Long Filename', () => {
+  const props = createProps({
+    attachments: [
+      {
+        contentType: 'text/plain' as MIMEType,
+        fileName:
+          'INSERT-APP-NAME_INSERT-APP-APPLE-ID_AppStore_AppsGamesWatch.psd.zip',
+        url: 'a2/a2334324darewer4234',
+      },
+    ],
+    status: 'sent',
+    text: 'This is what I have done.',
+  });
+
+  return renderBothDirections(props);
+});
+
 story.add('TapToView Image', () => {
   const props = createProps({
     attachments: [
diff --git a/ts/models/conversations.ts b/ts/models/conversations.ts
index c896e055e..bffc43a8f 100644
--- a/ts/models/conversations.ts
+++ b/ts/models/conversations.ts
@@ -2803,11 +2803,7 @@ export class ConversationModel extends window.Backbone.Model<
       return Promise.all(
         attachments
           .filter(
-            attachment =>
-              attachment &&
-              attachment.contentType &&
-              !attachment.pending &&
-              !attachment.error
+            attachment => attachment && !attachment.pending && !attachment.error
           )
           .slice(0, 1)
           .map(async attachment => {
diff --git a/ts/state/selectors/conversations.ts b/ts/state/selectors/conversations.ts
index f00bdb996..df6971687 100644
--- a/ts/state/selectors/conversations.ts
+++ b/ts/state/selectors/conversations.ts
@@ -424,7 +424,7 @@ export const getConversationSelector = createSelector(
       if (onE164) {
         return selector(onE164);
       }
-      const onUuid = getOwn(byUuid, id);
+      const onUuid = getOwn(byUuid, id.toLowerCase ? id.toLowerCase() : id);
       if (onUuid) {
         return selector(onUuid);
       }
diff --git a/ts/views/conversation_view.ts b/ts/views/conversation_view.ts
index b7466568c..df8836300 100644
--- a/ts/views/conversation_view.ts
+++ b/ts/views/conversation_view.ts
@@ -1372,8 +1372,15 @@ Whisper.ConversationView = Whisper.View.extend({
     const { files } = e.originalEvent.dataTransfer;
     for (let i = 0, max = files.length; i < max; i += 1) {
       const file = files[i];
-      // eslint-disable-next-line no-await-in-loop
-      await this.maybeAddAttachment(file);
+      try {
+        // eslint-disable-next-line no-await-in-loop
+        await this.maybeAddAttachment(file);
+      } catch (error) {
+        window.log.error(
+          'ConversationView/onDrop: Failed to add attachment:',
+          error && error.stack ? error.stack : error
+        );
+      }
     }
   },
 
@@ -1399,12 +1406,23 @@ Whisper.ConversationView = Whisper.View.extend({
 
     return {
       // In conversation model/redux
-      attachments: draftAttachments.map((attachment: any) => ({
-        ...attachment,
-        url: attachment.screenshotPath
-          ? getAbsoluteDraftPath(attachment.screenshotPath)
-          : getAbsoluteDraftPath(attachment.path),
-      })),
+      attachments: draftAttachments.map((attachment: any) => {
+        let url = '';
+        if (attachment.screenshotPath) {
+          url = getAbsoluteDraftPath(attachment.screenshotPath);
+        } else if (attachment.path) {
+          url = getAbsoluteDraftPath(attachment.path);
+        } else {
+          window.log.warn(
+            'getPropsForAttachmentList: Attachment was missing both screenshotPath and path fields'
+          );
+        }
+
+        return {
+          ...attachment,
+          url,
+        };
+      }),
       // Passed in from ConversationView
       onAddAttachment: this.onChooseAttachment.bind(this),
       onClickAttachment: this.onClickAttachment.bind(this),
@@ -1479,9 +1497,9 @@ Whisper.ConversationView = Whisper.View.extend({
       draftAttachments: [...draftAttachments, onDisk],
       draftChanged: true,
     });
-    await this.saveModel();
-
     this.updateAttachmentsView();
+
+    await this.saveModel();
   },
 
   async onCloseAttachment(attachment: any) {
@@ -1701,7 +1719,16 @@ Whisper.ConversationView = Whisper.View.extend({
       return;
     }
 
-    await this.addAttachment(attachment);
+    try {
+      await this.addAttachment(attachment);
+    } catch (error) {
+      window.log.error(
+        'Error saving draft attachment:',
+        error && error.stack ? error.stack : error
+      );
+
+      this.showToast(Whisper.UnableToLoadToast);
+    }
   },
 
   isSizeOkay(attachment: any) {