Mach-O executable Debug File not uploaded on first sentry-cli call

[InterstellarStella]

Environment

SaaS (https://sentry.io/)

Steps to Reproduce

1. Have a Mach-O executable and a Mach-O debug companion debug files in one folder
2. Upload them to Sentry through the following command:

sentry-cli upload-dif -o <org_slug> -p <proj_slug> --auth-token <auth_token> path/to/folder --log-level=debug

Expected Result

Both files are uploaded at the same time.

Actual Result

The terminal logs indicate that both files were uploaded.

However, only the Mach-O debug companion is uploaded.

Upon running the same command, the terminal logs indicate that there is nothing to upload

And that is when the Mach-O executable is actually uploaded on Sentry.

I ran this command twice with a 1 hour difference between the execution of the two:

Adding the full debug logs from both command executions in the linked internal ticket.

Product Area

Other

Link

https://dragonfruit-dev.sentry.io/settings/projects/unity/debug-symbols/

DSN

No response

Version

No response

┆Issue is synchronized with this Jira Improvement by Unito

[getsantry[bot]]

Assigning to @getsentry/support for routing ⏲️

[getsantry[bot]]

Failed to route for Product Area: Other. Defaulting to @getsentry/open-source for triage ⏲️

[github-actions[bot]]

This issue has gone three weeks without activity. In another week, I will close it.

But! If you comment or otherwise update it, I will reset the clock, and if you label it Status: Backlog or Status: In Progress, I will leave it alone ... forever!

---

"A weed is but an unloved flower." ― Ella Wheeler Wilcox 🥀

[github-actions[bot]]

This issue has gone three weeks without activity. In another week, I will close it.

But! If you comment or otherwise update it, I will reset the clock, and if you label it Status: Backlog or Status: In Progress, I will leave it alone ... forever!

---

"A weed is but an unloved flower." ― Ella Wheeler Wilcox 🥀

[loewenheim]

Apologies for the late reply , this completely slipped through the cracks. I can't manage to reproduce this; when I upload MachO debug files, everything happens at once.

[InterstellarStella]

Hi @loewenheim , I ran the command twice and one hour apart again. The first time, only the Mach-O debug companion (x86_64) was uploaded, and the second time, the missing Mach-O executable (x86_64) was uploaded. You can find them here.

[szokeasaurusrex]

Hi @InterstellarStella, I attempted to reproduce the issue with Sentry CLI 2.23.0, and similar to @loewenheim, both files were uploaded simultaneously for me. Could you please confirm whether you are still observing this issue with the latest Sentry CLI version?

[szokeasaurusrex]

Closing this issue, since I was unable to reproduce it, and the issue has been inactive since I asked for more information on how to reproduce the issue.

@InterstellarStella, if you are still observing this bug, please reopen the issue.