Prelude

This is a short story about how I configured myself out of my own email. Posting this as an exercise in humility, a tutorial for my future self in case of amnesia, and penance for my sins.

Background

• I have 2x Gmail accounts: work and personal.
• I configure work to send emails as personal.
• I configure personal to forward incoming emails to work.

This allows me to use work and manage both of my inboxes as one. I recently added two-factor authentication (2FA) to personal, forgot about it, and spent a few days unable to send personal emails from any work device.

Symptoms

Whenever I tried to send emails on behalf of personal, I'd receive the following error message as a reply:

You're sending this from a different address using the 'Send mail as' feature. The settings for your 'Send mail as' account are misconfigured or out of date. Check those settings and try resending.

Useful error message if you ask me (especially in retrospect), but because I had forgotten that I setup 2FA for personal, I naively assumed this issue might magically disappear given enough time... kind of how restarting your device resets the state and causes the symptoms of a certain class of bugs to disappear.

After a few days of mounting frustration, I decided to take a closer look...

Solution

• Create an "App Password" for personal: instructions.
• Login to work and delete personal from Settings > Accounts > Send mail as.
• Add another email address for personal using the "App Password" you just created.

And now I'm back in business!