I was replying to a gmail thread yesterday when a red box reading something like "gmail pop3 authentication error" appeared on the screen over the area where I should have seen a yellow "message sent" box.

When I clicked on the red box it took me to the gmail settings screen where another red box reads "Authentication error. Mail from this account has not been retrieved since 3/23/15." I'm familiar with this error. I have an old Outlook address forwarded to my gmail account, and I changed my Outlook password a while back and didn't update it in gmail.

The email I'm not sure was sent was the third message in the thread. I sent the first one, and I know it was delivered because it was responded to. I compared the header information of the message I know was received and the one I'm not sure of, and both are similar, no red flags. Both messages are also in my "Sent Mail" box. Still, the fact that that error popped up makes me wonder if the third message in the thread didn't get delivered.

Has anyone had experience with POP3 errors blocking gmail messages from being sent? Was the appearance of the POP3 error message maybe just a coincidence? Is there any way, using the header information for example, to verify whether or not there was an error in the sending of the third message?

EDIT: Here is a screenshot of the settings section. I wasn't able to grab a shot of the error message when I sent the message, but the red box is the same, and the message included something to the effect of "gmail pop3 authentication error":

4 Sorted by: Reset to default

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