When documentation cautions that something may not happen, that suggests that it normally does happen
TL;DR: If the troubleshooter documentation helps you fix a problem when X doesn’t occur, then this suggests that X normally occurs.
Someone reported on a peer support distribution list that running a particular internal tool appeared to hang, and they were hoping someone could help troubleshoot why.
In the Troubleshooting documentation for the internal tool, it says,
In some cases, the tool may fail the operation without prompting you for two factor authentication. If that is the case, then…
If you read between the lines, the documentation is suggesting that under normal conditions, the tool prompt for two factor authentication. It doesn’t come right out and say this, but given that it’s giving you a workaround if the two factor authentication prompt fails to appear, that means that people are expecting the prompt and not getting it.
My suggestion was to look around for a two factor authentication prompt, possibly covered by another window. My guess is that the tool is waiting to complete an authentication flow.