"Unable to retrieve app-specific password on a different Mac: once an app specific password created, I am unable to subsequently retrieve it when using the same app on a different Mac."
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Two-Factor Authentication for App:
If this app is in your Apple Account, then add this Mac as a Trusted Device --you should then get this. Some apps (i.e. Outlook) have THEIR OWN apps for logging in. Go here: Add or remove trusted devices on Mac - Apple Support
See your Devices:
Verify that your Mac is associated to your account, by going here: http://icloud.com/find