# PDF File Sync Issue Between iPhone and Mac - App Crashes When Right Click the pdf

**URL:** <https://community.bear.app/t/pdf-file-sync-issue-between-iphone-and-mac-app-crashes-when-right-click-the-pdf/15187>\
**Category:** Bear Bug Report\
**Created:** [February 18, 2025, 4:17pm UTC](https://community.bear.app/t/pdf-file-sync-issue-between-iphone-and-mac-app-crashes-when-right-click-the-pdf/15187 "2025-02-18T16:17:02Z")\
**Posts on this page:** 3\
**Page:** 1

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**Author:** ![binbinsh](https://avatars.discourse-cdn.com/v4/letter/b/cdc98d/32.png) [@binbinsh](https://community.bear.app/u/binbinsh)\
**Post date:** [February 18, 2025, 4:17pm UTC](https://community.bear.app/t/pdf-file-sync-issue-between-iphone-and-mac-app-crashes-when-right-click-the-pdf/15187/1 "2025-02-18T16:17:02Z")

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- **Bear Version** : 2.3.10 (13092)
- **OS Version** : Sequoia 15.3.1, iOS 18.3.1

**What were you doing** :  
I was trying to add a new PDF file to an existing note on my iPhone. The note already contained multiple PDF files.

**What feature did you use** :

- PDF file attachment
- iCloud sync between iPhone and Mac

**What happened** :

1. Successfully added and opened the new PDF file on iPhone
2. All other PDFs in the note synced correctly to Mac
3. The newly added PDF failed to sync to Mac
4. When trying to right-click the PDF file on Mac, Bear app crashes

**What did you expect to happen** :

The new PDF file should sync from iPhone to Mac and be accessible/viewable on both devices, just like the other PDF files in the note.

**Additional Information** :

- The crash only occurs with this specific newly added PDF
- Other PDF files in the same note work normally
- The sync issue only affects this particular PDF file newly added from iPhone
- All other note content syncs correctly between devices

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**Author:** ![binbinsh](https://avatars.discourse-cdn.com/v4/letter/b/cdc98d/32.png) [@binbinsh](https://community.bear.app/u/binbinsh)\
**Post date:** [February 20, 2025, 8:19am UTC](https://community.bear.app/t/pdf-file-sync-issue-between-iphone-and-mac-app-crashes-when-right-click-the-pdf/15187/2 "2025-02-20T08:19:56Z")

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One more information: the PDF file sync correctly to iPad, I can open the PDF file in iPad Pro, but cannot open it on Mac.

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**Author:** ![trix180](https://dub1.discourse-cdn.com/flex013/user_avatar/community.bear.app/trix180/32/588_2.png) [@trix180](https://community.bear.app/u/trix180)\
**Post date:** [February 20, 2025, 8:45am UTC](https://community.bear.app/t/pdf-file-sync-issue-between-iphone-and-mac-app-crashes-when-right-click-the-pdf/15187/3 "2025-02-20T08:45:41Z")

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Please write our customer service, we need to ask for crash logs.

> **[Bear](https://bear.app/contact/)**
>
> Customer Support. Contact Us For Help or Information