Outlook doesn’t realize that that’s not going to get fixed and treats it like any transient error that might not happen if it tries again. You start sending your 24.5 megabyte behemoth, and five megabytes in your ISP’s mailer says “Nope, too big – FAIL”. Let’s say your ISP has a cap of five megabytes on email message size. Surprisingly, the most low-tech solution is what I’ve found to be the most effective. There are a couple of ways to deal with this issue. Your ISP rejects the email because it’s too big, only to have Outlook keep trying to send the mail because it doesn’t realize that the error is fatal. It’s been a while, but I’ve experienced this myself.
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