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Outlook not sending to some recipients

Posted on 2014-08-27
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Last Modified: 2014-11-12
Hi Guys

I have a client who is using Outlook 2013 on Windows 8, they have Google apps (Gmail). She is complaining that some people from different companies "sometimes" don't get her emails when using Outlook, no errors, no bounce backs.

However if she uses the browser she has no problems. Other people in the office can send and receive to people she is having problems with, so it's not blacklists or anything like that.

It happens whether it is a new email or if she responds to an email.

Any ideas?
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Question by:Ergs
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by:Trenton Knew
ID: 40289172
dumb question, is she attempting to send messages with no subject or body sometimes?  Does the computer have a spam filter installed?
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Author Comment

by:Ergs
ID: 40289185
No always has subject and body, they are a business so they are official/professional emails.

What do you mean computer having spam filters? There are no email servers or anything like that in the office so the only spam filters would be the standard stuff in Outlook.
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by:Trenton Knew
ID: 40289206
do her messages make it to  a sent folder?  can they be seen in the web interface if sent from outlook?
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by:McKnife
ID: 40289227
You have no reproducible error, this cannot be solved theoretically in a forum. You need to use tracing.
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bas2754 earned 1500 total points
ID: 40289374
Is the account setup to use IMAP or POP3?  Outlook 2013 is buggy at best with it's IMAP support and it is entirely possible (though not likely) these problems could be related. Are all the latest patches installed?   Is there AV software that is doing outbound scanning that might be blocking these messages?

You might try switching to POP3 (not my favorite solution, but it works better in my experience) and see if that does better.  Theoretically it should not matter as they both use SMTP to send.  The problems with IMAP are usually in the way messages are copied to other folders and not synching up.

You may also be dealing with a case of the emails just were never sent.  We had a client put tickets in several times saying email they sent was never received, however we finally tracked it down to the fact that the person had missed deadlines and never sent the emails and the tickets were put in to cover their rear end and give an excuse.  This took lots of hours since we hosted the mail server and lots of logging and reviewing of logs to finally prove it.  In the end they came clean.

Not saying that is what is happening in this case, just that it has happened.  You can try opening a support case with Gmail if you can find the specific date / timestamp of an email that was for sure sent and never received.  It could also be the recipient's server seeing the internal or external IP of the sending client and rejecting the message via Anti-Spam software (seen that one more than once as well).  Heck we even had once customer who could never send messages because their last name had a curse word in it if you took the letters before and after it out.

Bottom line is you are going / or the client is going to have to spend a fair amount of time tracking this down.  I would lean mostly towards something in the message header causing the message to get blocked at the other end.  You may also contact the other mail administrator and see if they can check their logs for what might have occurred.

Let us know if you need further assistance.
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by:bas2754
ID: 40289380
One other suggestion:  Have the user start to CC' his or herself on every message.  These can be moved easily by looking for messages From the user using a rule so it won't clutter the inbox.  What it will do, however is ensure the message at least made it to the Gmail server.  Then if a message does not go through you can at least determine if it got to Gmail.
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Author Closing Comment

by:Ergs
ID: 40294949
Bas2754 I will except your answer.
They are using IMAP, not sure of Google mail will work with POP? Either way, it may be issues with Outlook 2013 and updates.... otherwise I will need to be onsite and spend a bit of time on "tracing" this problem (if it exists)

Thanks.
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