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I've discovered that my Mac can't fetch software updates because the requests to Apple server's are failing. I think it's something related to HTTPS cert validating or cert pinning. I was tipped off to this when my attempts to download additional Accessibility Speech voices failed, but now I realize that all official Apple software updates are failing including macOS updates. Updating 3rd party App Store apps works fine though.

Looking at the console logs for the softwareupdated process shows some error messages. trustd also shows some messages about fetching certs and seem to report some errors. The failures are all related to attempting to fetch data from Apple's servers. It tries many times but all the requests eventually fail and and softwareupdated reports this error message in the logs: HTTP load failed (error code: -999 [1:89])

Any idea what could be causing this? I'm not MITMing Apple's traffic and when I try to access the same URL's softwareupdated is accessing (https://swdist.apple.com/content/downloads/04/56/091-98955/5rqoo0g007lq35tjt64dow68kiwa1zr8qo/091-98955.English.dist) with curl/wget/safari/chrome it all works fine. Its HTTPS certs seem fine as well. Given how many minor version of macOS I'm behind I suspect this has been happening ever since I set up my new Mac Mini in November. It was set up by restoring from a time machine backup of another computer so whatever is causing this was probably copied along with the backup.

I have a 2018 Mac Mini running macOS 10.14 (but will manually update to 10.14.3 now). I'm a developer with a bit of security focus so have a variety of 3rd party software installed on my system but nothing obvious that could explain this. No non-Apple kext's are running beside Dropbox's.

trustd errors. These are interpersed with softwareupdated's

default 16:49:58.876053 -0800   trustd  cert[2]: AnchorTrusted =(leaf)[force]> 0
default 16:49:59.159392 -0800   trustd  asynchronously fetching CRL (http://crl.apple.com/root.crl) for client (tccd[255]/0#-1 LF=0)
default 16:49:59.159442 -0800   trustd  cert[2]: AnchorTrusted =(leaf)[force]> 0
default 16:50:05.180018 -0800   trustd  cert[2]: AnchorTrusted =(leaf)[force]> 0
default 16:50:05.298422 -0800   trustd  cert[2]: AnchorTrusted =(leaf)[force]> 0
default 16:50:05.303718 -0800   trustd  cert[2]: AnchorTrusted =(leaf)[force]> 0
default 16:50:20.205432 -0800   trustd  could not enable test hierarchy: no UAT pinning preferences set
default 16:50:34.043370 -0800   trustd  could not enable test hierarchy: no UAT pinning preferences set

softwareupdated's

error   16:50:34.304316 -0800   softwareupdated Task <A2B113E7-AD89-4C7E-BE56-F7D8ECA477FB>.<0> HTTP load failed (error code: -999 [1:89])
default 16:50:34.304763 -0800   softwareupdated TIC Enabling TLS [1013:0x7fa8aa149430]
default 16:50:34.304812 -0800   softwareupdated TIC TCP Conn Start [1013:0x7fa8aa149430]
default 16:50:34.304907 -0800   softwareupdated [C1013 Hostname#faa5b06f:443 tcp, url: https://swdist.apple.com/content/downloads/44/49/zzz031-12188/hqitb6xvqf7pmgevm58rczqxejtm12i13t/SecUpd2011-004.dst/031-, tls] start
default 16:50:34.305287 -0800   softwareupdated nw_connection_report_state_with_handler_locked [C1013] reporting state preparing
default 16:50:34.305883 -0800   softwareupdated Task <9F000744-FC4E-435C-B0CC-949938C6EA68>.<0> setting up Connection 1013
default 16:50:34.337754 -0800   softwareupdated nw_socket_handle_socket_event [C1013.1:3] Socket received CONNECTED event
default 16:50:34.337862 -0800   softwareupdated nw_endpoint_flow_protocol_connected [C1013.1 IPv4#4ca64c91:443 in_progress socket-flow (satisfied)] Transport protocol connected
default 16:50:34.338976 -0800   softwareupdated TIC TLS Event [1013:0x7fa8aa149430]: 1, Pending(0)
default 16:50:34.339075 -0800   softwareupdated TIC TLS Event [1013:0x7fa8aa149430]: 2, Pending(0)
default 16:50:34.374307 -0800   softwareupdated TIC TLS Event [1013:0x7fa8aa149430]: 2, Pending(0)
default 16:50:34.374384 -0800   softwareupdated TIC TLS Event [1013:0x7fa8aa149430]: 11, Pending(0)
default 16:50:34.374474 -0800   softwareupdated TIC TLS Event [1013:0x7fa8aa149430]: 14, Pending(0)
default 16:50:34.380009 -0800   softwareupdated TIC TCP Conn Cancel [1013:0x7fa8aa149430]
default 16:50:34.380075 -0800   softwareupdated [C1013 Hostname#faa5b06f:443 tcp, url: https://swdist.apple.com/content/downloads/44/49/zzz031-12188/hqitb6xvqf7pmgevm58rczqxejtm12i13t/SecUpd2011-004.dst/031-, tls] cancel
default 16:50:34.380106 -0800   softwareupdated [C1013 Hostname#faa5b06f:443 tcp, url: https://swdist.apple.com/content/downloads/44/49/zzz031-12188/hqitb6xvqf7pmgevm58rczqxejtm12i13t/SecUpd2011-004.dst/031-, tls] cancelled
default 16:50:34.380134 -0800   softwareupdated 0.000s [C1013 <private> Hostname#faa5b06f:443 resolver] path:start
default 16:50:34.380161 -0800   softwareupdated 0.000s [C1013 <private> Hostname#faa5b06f:443 resolver] path:satisfied
default 16:50:34.380182 -0800   softwareupdated 0.000s [C1013 <private> Hostname#faa5b06f:443 resolver] resolver:start_dns
default 16:50:34.380198 -0800   softwareupdated 0.001s [C1013 <private> Hostname#faa5b06f:443 resolver] resolver:receive_dns
default 16:50:34.380232 -0800   softwareupdated 0.001s [C1013.1 <private> 192.168.86.30:50676<->IPv4#4ca64c91:443 socket-flow] path:start
default 16:50:34.380252 -0800   softwareupdated 0.002s [C1013.1 <private> 192.168.86.30:50676<->IPv4#4ca64c91:443 socket-flow] path:satisfied
default 16:50:34.380269 -0800   softwareupdated 0.003s [C1013.1 <private> 192.168.86.30:50676<->IPv4#4ca64c91:443 socket-flow] flow:start_connect
default 16:50:34.380287 -0800   softwareupdated 0.032s [C1013.1 <private> 192.168.86.30:50676<->IPv4#4ca64c91:443 socket-flow] flow:finish_transport
default 16:50:34.380303 -0800   softwareupdated 0.033s [C1013 <private> Hostname#faa5b06f:443 resolver] flow:finish_transport
default 16:50:34.380373 -0800   softwareupdated 0.075s [C1013] path:cancel
default 16:50:34.380560 -0800   softwareupdated nw_endpoint_flow_protocol_disconnected [C1013.1 IPv4#4ca64c91:443 cancelled socket-flow (null)] Output protocol disconnected
default 16:50:34.380618 -0800   softwareupdated nw_connection_report_state_with_handler_locked [C1013] reporting state cancelled
default 16:50:34.380677 -0800   softwareupdated Task <DFA3454A-C4D6-4EE1-A6B0-04E1B6C60358>.<0> {strength 0, tls 4, ct 0, sub 0, sig 1, ciphers 0, bundle 1, builtin 0}
default 16:50:34.380738 -0800   softwareupdated TIC TCP Conn Destroyed [1013:0x7fa8aa149430]
error   16:50:34.380765 -0800   softwareupdated Task <9F000744-FC4E-435C-B0CC-949938C6EA68>.<0> HTTP load failed (error code: -999 [1:89])
default 16:50:34.381192 -0800   softwareupdated TIC Enabling TLS [1014:0x7fa8a27b0ef0]
default 16:50:34.381243 -0800   softwareupdated TIC TCP Conn Start [1014:0x7fa8a27b0ef0]
default 16:50:34.381340 -0800   softwareupdated [C1014 Hostname#faa5b06f:443 tcp, url: https://swdist.apple.com/content/downloads/04/56/091-98955/5rqoo0g007lq35tjt64dow68kiwa1zr8qo/091-98955.English.dist, tls] start
default 16:50:34.381629 -0800   softwareupdated nw_connection_report_state_with_handler_locked [C1014] reporting state preparing
default 16:50:34.382202 -0800   softwareupdated Task <DFA3454A-C4D6-4EE1-A6B0-04E1B6C60358>.<0> setting up Connection 1014
default 16:50:34.416189 -0800   softwareupdated nw_socket_handle_socket_event [C1014.1:3] Socket received CONNECTED event
default 16:50:34.416259 -0800   softwareupdated nw_endpoint_flow_protocol_connected [C1014.1 IPv4#4ca64c91:443 in_progress socket-flow (satisfied)] Transport protocol connected
default 16:50:34.417047 -0800   softwareupdated TIC TLS Event [1014:0x7fa8a27b0ef0]: 1, Pending(0)
default 16:50:34.417117 -0800   softwareupdated TIC TLS Event [1014:0x7fa8a27b0ef0]: 2, Pending(0)
default 16:50:34.452126 -0800   softwareupdated TIC TLS Event [1014:0x7fa8a27b0ef0]: 2, Pending(0)
default 16:50:34.452828 -0800   softwareupdated TIC TLS Event [1014:0x7fa8a27b0ef0]: 11, Pending(0)
default 16:50:34.452900 -0800   softwareupdated TIC TLS Event [1014:0x7fa8a27b0ef0]: 14, Pending(0)
default 16:50:34.458266 -0800   softwareupdated TIC TCP Conn Cancel [1014:0x7fa8a27b0ef0]
default 16:50:34.458321 -0800   softwareupdated [C1014 Hostname#faa5b06f:443 tcp, url: https://swdist.apple.com/content/downloads/04/56/091-98955/5rqoo0g007lq35tjt64dow68kiwa1zr8qo/091-98955.English.dist, tls] cancel
default 16:50:34.458348 -0800   softwareupdated [C1014 Hostname#faa5b06f:443 tcp, url: https://swdist.apple.com/content/downloads/04/56/091-98955/5rqoo0g007lq35tjt64dow68kiwa1zr8qo/091-98955.English.dist, tls] cancelled
default 16:50:34.458370 -0800   softwareupdated 0.000s [C1014 <private> Hostname#faa5b06f:443 resolver] path:start
default 16:50:34.458393 -0800   softwareupdated 0.000s [C1014 <private> Hostname#faa5b06f:443 resolver] path:satisfied
default 16:50:34.458410 -0800   softwareupdated 0.000s [C1014 <private> Hostname#faa5b06f:443 resolver] resolver:start_dns
default 16:50:34.458427 -0800   softwareupdated 0.001s [C1014 <private> Hostname#faa5b06f:443 resolver] resolver:receive_dns
default 16:50:34.458465 -0800   softwareupdated 0.001s [C1014.1 <private> 192.168.86.30:50677<->IPv4#4ca64c91:443 socket-flow] path:start
default 16:50:34.458489 -0800   softwareupdated 0.001s [C1014.1 <private> 192.168.86.30:50677<->IPv4#4ca64c91:443 socket-flow] path:satisfied
default 16:50:34.458507 -0800   softwareupdated 0.002s [C1014.1 <private> 192.168.86.30:50677<->IPv4#4ca64c91:443 socket-flow] flow:start_connect
default 16:50:34.458541 -0800   softwareupdated 0.034s [C1014.1 <private> 192.168.86.30:50677<->IPv4#4ca64c91:443 socket-flow] flow:finish_transport
default 16:50:34.458575 -0800   softwareupdated 0.034s [C1014 <private> Hostname#faa5b06f:443 resolver] flow:finish_transport
default 16:50:34.458627 -0800   softwareupdated 0.076s [C1014] path:cancel
default 16:50:34.459008 -0800   softwareupdated nw_endpoint_flow_protocol_disconnected [C1014.1 IPv4#4ca64c91:443 cancelled socket-flow (null)] Output protocol disconnected
default 16:50:34.459116 -0800   softwareupdated nw_connection_report_state_with_handler_locked [C1014] reporting state cancelled
default 16:50:34.459184 -0800   softwareupdated Task <0E99010F-D266-4894-AAD3-9C00BEA0A1AE>.<0> {strength 0, tls 4, ct 0, sub 0, sig 1, ciphers 0, bundle 1, builtin 0}
default 16:50:34.459266 -0800   softwareupdated TIC TCP Conn Destroyed [1014:0x7fa8a27b0ef0]
error   16:50:34.459290 -0800   softwareupdated Task <DFA3454A-C4D6-4EE1-A6B0-04E1B6C60358>.<0> HTTP load failed (error code: -999 [1:89])

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