Request Timed Out on first couple of attempts to connect to a server after authorization

[pvachon]

I have an intermittent issue that happens on Linux and macOS X Mojave, where the response from my phone seems to get lost in the ether.

When I connect to a host, I'll always see krssh specifying it is requesting authorization from my phone. My phone receives the push notification within seconds, and I grant permission to connect. However, after that, krssh seems to receive nothing, and times out, falling back to local keys. If I let the whole ssh connection attempt time out, then the next attempt to authorize using Krypton succeeds end-to-end.

This happens a few times, especially seemingly with freshly started shells. When I start ssh with a high level of verbosity, the log output tails off after krssh takes over.

The relevant output from Krypton:

Krypton ▶ Requesting SSH authentication from phone
Krypton ▶ Phone approval required. Respond using the Krypton app
Krypton ▶ Request timed out. Make sure your phone and workstation are paired and connected to the internet and the Krypton app is running.
Krypton ▶ Falling back to local keys.

[pvachon]

Just a further update -- this seems worse when I approve a connection using my Apple Watch. I've also found if I approve a connection using my Apple Watch, then kill the Krypton app on my phone and restart it, it seems to approve the connection. Maybe this is something between the Apple Watch and Krypton occasionally?