Email not sent

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Jeff

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My wife has Outlook 2003 on a Windows 7 machine and uses AOL (pop) email. Recently, we have discovered a very weird problem. On emails that she sends (to me or her daughter, for instance), they go into her "sent" folder but they never arrive (my email is comcast and her daughter has a work and home email). She does not get any notification of the failed delivery. Additionally, if she composes an email to herself, it arrives fine. Also, if she replies to an email from me, that reply arrives fine. If she takes an email and forwards it to someone, it arrives without any problem. The issue seems to be isolated to her composing and sending an original email to anyone other than herself.

I have looked all over to try to find a solution to this but nothing has worked. I restored her system back before the problem began (a number of windows updates occurred), and created a new outlook profile for the same aol email and that didn't work.

Any suggestions?
 

Diane Poremsky

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Jeff

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Thanks for the help but autocomplete was not the problem. I had her use the address book and type in the full email ID instead of autocomplete and she gets the same result. She can send email to herself and can reply or forward emails to people but original emails sent to anyone other than herself show in Outlook 2003 as being "sent", she gets no failure notification and the recipients never get the emails. I was suspicious of the fact that this started happening shortly after AOL made changes in there email process to reduce spam and spoofing of email and have been in contact with AOL tech people who don't think it's related.

I am now wondering if this might be unique to her combination of Outlook 2003 and Windows 7. I created an AOL email id and set it up on my own Windows XP PC with Outlook 2003 and everything works fine, so it doesn't seem to be an ISP issue (Comcast in our case).
 

Jeff

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Ooops...just found out that I can recreate the problem with my own AOL email id on a different PC. I created an AOL profile in Outlook 2003 on a Windows XP PC and the same exact problem occurs: original emails appear to have been sent but do not get through and there is no failure notification. However, replies or emails that are forwarded do get sent and received as well as emails I send to myself.

I called my ISP (Comcast) and they don't think the issue is with them. That only leaves 2 variables - Outlook 2003 and AOL. AOL just recently made changes to their email processes related to reducing SPAM (DMARC/DKIM policy related) and I think this problem is related to that but I cannot find any info anywhere else to confirm and AOL doesn't respond. I think, because she is not using AOL's email servers initially (must be routing from Outlook through Comcast email servers to AOL) that, for some reason, these original emails are failing the spam test and get thrown away but forwarded or replied emails do not fail the spam test and get through. It might be something in Outlook 2003, I suppose though.
 

Diane Poremsky

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The spam test should affect both new messages and replies because they'd both use the same server. Granted, a reply has more content and should look less spammy, but that is no guarantee (I'm always fishing mail from an insurance salesman client out of the junk folder, even replies.) Usually, when a server is blacklisted, only mail to specific addresses is affected - as in those addresses using the filter, so I'd expect some messages to get through.

I know one of the antivirus suites - AVG I think - tends to filter mail sent to blacklisted servers, so if you use security software that filters mail, try disabling it. In the meantime, I'll dust off my AOL address and see if I can repro.
 

Jeff

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One possibility - I have looked at recommended AOL settings for various Outlook versions (2003, 2007, 2010, etc.). They are not consistent at all but in the recommended settings for Outlook 2007 (I think that was the one), they had recommended setting up outbound server encryption of TLS and Outlook 2003 only seems to support SSL (or nothing). That might be the problem, which would mean having to upgrade Outlook. Not sure I want to do that. Maybe I will finally convince my wife to exit AOL mail now and use something else (GMAIL or Comcast's or...)
 

Diane Poremsky

Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
Office 365 Exchange
I don't think tls/ssl matters, if it did, the message shouldn't send at all. But I'll test it on my 2003 test system and see if i an repro. That's not to say switching to a better service isn't a good idea. :) I'd recommend gmail or outlook.com over Comcast, only because it doesn't tie you to the internet provider.
 
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