I’m also experiencing this issue with failed uploads to files.oaiusercontent.com on my Mac, running macOS Sequoia 15.1 beta. This problem started yesterday, and so far, I’ve been unable to resolve it.
Issue Details:
Affected Device: Mac running macOS Sequoia 15.1 beta.
Unaffected Device: I’ve tested this on another laptop (different OS), and the issue does not occur there.
Internet Connections: I’ve tried multiple ISPs (my regular internet and a mobile hotspot) but can reproduce the issue on both with my Mac.
Firewall Suspected: Since the issue persists across different ISPs but only on my Mac, I suspect that something on the OS (possibly a firewall or network security setting) is blocking the upload process.
Troubleshooting Steps Taken:
Tested on Different Devices: I was able to upload files successfully on another laptop.
Tried Different Networks: Tested using my home internet and mobile hotspot but encountered the same issue on the Mac.
Network Path Check (Traceroute): Below is the traceroute output from my Mac. It seems to be reaching the server without issues, but file uploads still fail:
$ traceroute files.oaiusercontent.com
traceroute: Warning: files.oaiusercontent.com has multiple addresses; using 104.18.43.204
traceroute to files.oaiusercontent.com (104.18.43.204), 64 hops max, 40 byte packets
1 192.168.0.1 (192.168.0.1) 50.405 ms 3.989 ms 4.323 ms
2 * * *
3 [REDACTED] (86.28.65.93) 12.960 ms 11.316 ms 12.458 ms
4 * * *
5 [REDACTED] (62.253.174.178) 12.729 ms 12.358 ms 18.218 ms
6 162.158.32.254 (162.158.32.254) 12.469 ms 23.490 ms 23.389 ms
7 162.158.32.9 (162.158.32.9) 12.303 ms 13.861 ms
162.158.32.11 (162.158.32.11) 12.874 ms
8 104.18.43.204 (104.18.43.204) 12.635 ms 11.261 ms 12.839 ms
This shows that my Mac can reach the file server, but the issue seems to be related to something internal, possibly a firewall or macOS security configuration.
Additional Context:
I suspect that FileVault or some other macOS-specific security mechanism could be interfering with the upload process.
I’ve tried standard troubleshooting steps such as disabling firewalls and testing with different browsers, but the issue persists.
Request:
If anyone has encountered a similar issue or can suggest further troubleshooting steps—especially around macOS Sequoia 15.1 beta—it would be greatly appreciated!
My issue is now resolved. I turned off the Mac firewall and tried uploading it worked.
I also tried a negative test to isolate what was the cause so I turned the firewall back again to see if it stops working but it didn’t. So literally no idea how I solved it.
But sharing this information if it helps anyone else.
same issue here. Not a company managed PC (private, windows). And i have extensive experience with networking, there is nothing being blocked internally.
i believe this might be issue on chatgpts end?
edit: its not resolved , not sure if its chatgpt fixing.
all i did was clear all my “memory” logg (under settings → personilization → clear memory)
(this deletes memory btw, not sure why it should save them when i deleted all my chats…).
I did not experience this is before, but after changing one of the settings of my GPT this problem started occuring. After turning the setting of again the problem seems resolved. Go to configure, scroll down to possibilities and turn of the bottom of the 3 checkboxes that entails code-interpretation and data-analysis (I am translating based on my Dutch version). Not sure this is a full solution for most of you, as it does mean the GPT has less capabilities.