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How to send emails like a pro
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Has so far included content from Warsandpeas, Mr. Lovenstein, SMBC, Loading Artist, Low Quality Facts, nixCraft, ElleGray, and other interesting or provocative stuff I've random'd across on Mastodon.
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One of the ways it happens is if you initiate “new email” from another program (say by clicking on an email address) while Outlook is closed.
It will sit in your outbox until you open Outlook properly.
If you also have that rule, I’m not sure if it creates further delay or some other conflict.