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Docker registry timeouts

I’m experiencing intermittent timeouts when authenticating to a private registry.

Authenticating with existing credentials...
Login did not succeed, error: Error response from daemon: Get https://registry.kio.to/v2/: net/http: request canceled while waiting for connection (Client.Timeout exceeded while awaiting headers)

I can verify that the registry is available, and the issue seems to go away for a while if I restart the docker daemon(but always comes back). The timeouts can also go away on their own after I retry enough time.

$ docker info
Client:
 Debug Mode: false

Server:
 Containers: 51
  Running: 11
  Paused: 0
  Stopped: 40
 Images: 1702
 Server Version: 19.03.8
 Storage Driver: overlay2
  Backing Filesystem: <unknown>
  Supports d_type: true
  Native Overlay Diff: true
 Logging Driver: json-file
 Cgroup Driver: cgroupfs
 Plugins:
  Volume: local
  Network: bridge host ipvlan macvlan null overlay
  Log: awslogs fluentd gcplogs gelf journald json-file local logentries splunk syslog
 Swarm: active
  NodeID: yo572uno2bjd53oadxthtuj6y
  Is Manager: true
  ClusterID: chd5fbuc27ylp459zgqurtjav
  Managers: 1
  Nodes: 1
  Default Address Pool: 10.0.0.0/8  
  SubnetSize: 24
  Data Path Port: 4789
  Orchestration:
   Task History Retention Limit: 5
  Raft:
   Snapshot Interval: 10000
   Number of Old Snapshots to Retain: 0
   Heartbeat Tick: 1
   Election Tick: 10
  Dispatcher:
   Heartbeat Period: 5 seconds
  CA Configuration:
   Expiry Duration: 3 months
   Force Rotate: 0
  Autolock Managers: false
  Root Rotation In Progress: false
  Node Address: 10.91.12.7
  Manager Addresses:
   10.91.12.7:2377
 Runtimes: runc
 Default Runtime: runc
 Init Binary: docker-init
 containerd version: 7ad184331fa3e55e52b890ea95e65ba581ae3429
 runc version: dc9208a3303feef5b3839f4323d9beb36df0a9dd
 init version: fec3683
 Security Options:
  apparmor
  seccomp
   Profile: default
 Kernel Version: 5.4.7-050407-generic
 Operating System: Ubuntu 18.04.4 LTS
 OSType: linux
 Architecture: x86_64
 CPUs: 8
 Total Memory: 15.49GiB
 Name: R90R4K4C
 ID: G3YQ:OF5B:5PRY:X5MO:YFBO:DYY4:VS44:U3HY:CV5Y:EXLS:U2ML:PT3M
 Docker Root Dir: /var/lib/docker
 Debug Mode: false
 Registry: https://index.docker.io/v1/
 Labels:
 Experimental: false
 Insecure Registries:
  127.0.0.0/8
 Live Restore Enabled: false