Hi Quinn,
I enabled CFNETWORK_DIAGNOSTICS and inspected the logs.
At the beggining of the request i can clearly see the timeouts set correctly in the paranthesis.
default 23:00:36.916759+0300 nsurlsessiond Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> resuming, timeouts(300.0, 300.0) QOS(0x19) Voucher <OS_voucher: 0x7f94a61086e0>
and the request sent without any error logging
default 23:00:37.264507+0300 nsurlsessiond Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> sent request, body S 104857891
and after 65 second
error 23:01:42.265141+0300 nsurlsessiond Connection 27: timed out with error(4:-2104)
error 23:01:42.265310+0300 nsurlsessiond Connection 27: encountered error(4:-2104)
default 23:01:42.265377+0300 nsurlsessiond Connection 27: cleaning up
so this error(4:-2104) could be usefull but i dont know what it is
and more errors and logs about retry
default 23:01:42.265482+0300 nsurlsessiond [C27 A6343939-91A0-4B91-9802-215D32D4A003 [REDACTED]:443 tcp, url hash: c6b386c1, traffic class: 200, expected workload: 1000, tls, indefinite] cancel
default 23:01:42.265688+0300 nsurlsessiond [C27 A6343939-91A0-4B91-9802-215D32D4A003 [REDACTED]:443 tcp, url hash: c6b386c1, traffic class: 200, expected workload: 1000, tls, indefinite] cancelled
[C27.1 B47D4C9A-ACE2-4C49-96C8-34C455DA4F13 127.0.0.1:54234<->127.0.0.1:9090]
Connected Path: satisfied (Path is satisfied), viable, interface: lo0
Duration: 65.346s, TCP @0.007s took 0.000s, TLS 1.3 took 0.013s
bytes in/out: 1870/105001218, packets in/out: 2/8268, rtt: 0.000s, retransmitted bytes: 0, out-of-order bytes: 0
default 23:01:42.266462+0300 nsurlsessiond nw_flow_disconnected [C27.1 127.0.0.1:9090 cancelled socket-flow ((null))] Output protocol disconnected
default 23:01:42.266762+0300 nsurlsessiond nw_connection_report_state_with_handler_on_nw_queue [C27] reporting state cancelled
default 23:01:42.267240+0300 nsurlsessiond Connection 27: done
default 23:01:42.267585+0300 nsurlsessiond Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> can retry(N) with reason(2) for error [4:-2104]
default 23:01:42.267621+0300 nsurlsessiond Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> RELEASING power assertion.
error 23:01:42.267673+0300 nsurlsessiond Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> HTTP load failed, 104859603/0 bytes (error code: -1001 [4:-2104])
default 23:01:42.268085+0300 nsurlsessiond Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> summary for task failure {transaction_duration_ms=65350, response_status=0, connection=27, protocol="http/1.1", domain_lookup_duration_ms=0, connect_duration_ms=0, secure_connection_duration_ms=0, request_start_ms=22, request_duration_ms=324, response_start_ms=0, response_duration_ms=0, request_bytes=104859603, response_bytes=0, cache_hit=0}
error 23:01:42.268480+0300 nsurlsessiond Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> finished with error [-1001] Error Domain=NSURLErrorDomain Code=-1001 "The request timed out." UserInfo={_kCFStreamErrorCodeKey=-2104, NSUnderlyingError=0x7f94a610bda0 {Error Domain=kCFErrorDomainCFNetwork Code=-1001 "(null)" UserInfo={NSErrorPeerAddressKey=<CFData 0x7f94a60267c0 [0x7fff8004b340]>{length = 16, capacity = 16, bytes = 0x100223827f0000010000000000000000}, _kCFStreamErrorCodeKey=-2104, _kCFStreamErrorDomainKey=4}}, _NSURLErrorFailingURLSessionTaskErrorKey=LocalUploadTask <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3>, _NSURLErrorRelatedURLSessionTaskErrorKey=(
"LocalUploadTask <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3>"
), NSLocalizedDescription=The request timed out., NSErrorFailingURLStringKey=https://[REDACTED]/s3/upload-file, NSErrorFailingURLKey=https://[REDACTED]/s3/upload-file, _kCFStreamErrorDomainKey=4}
default 23:01:42.268615+0300 nsurlsessiond NDSession <FD814BB3-5B2C-4D3A-9526-F250F73C2029> Task <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3> for client [REDACTED]will be retried after error Error Domain=NSURLErrorDomain Code=-1001 "The request timed out." UserInfo={_kCFStreamErrorCodeKey=-2104, NSUnderlyingError=0x7f94a610bda0 {Error Domain=kCFErrorDomainCFNetwork Code=-1001 "(null)" UserInfo={NSErrorPeerAddressKey=<CFData 0x7f94a60267c0 [0x7fff8004b340]>{length = 16, capacity = 16, bytes = 0x100223827f0000010000000000000000}, _kCFStreamErrorCodeKey=-2104, _kCFStreamErrorDomainKey=4}}, _NSURLErrorFailingURLSessionTaskErrorKey=LocalUploadTask <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3>, _NSURLErrorRelatedURLSessionTaskErrorKey=(
"LocalUploadTask <5C4414F6-6D5B-46D0-ACBA-E220B2607F14>.<3>"
after that request sent again and timed out again sent again... basically stucks in a loop.
so client thinks the request timed out at 65 seconds altough it has set the timeouts as 300 seconds correctly. And when i inspected http traffic at T+65 seconds server did not send any response or timeout.
PS: some addresses in logs are redacted by me