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Outlook 2010 causing emails to disappear


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#1 seg42

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Posted 23 June 2014 - 03:07 PM

For the past couple of weeks I've had a user come up with a strange error.

 

We have Exchange 2007, and she is using outlook 2010 on windows 7 64 bit.

 

Some emails are not reaching her inbox, but there seems to be no reason as to what emails, or some will come in one day, but not the next.

 

According to the exchange server, the emails are getting coming in like usual, but they are not appearing on her machine. If I open her webmail after she should have received these emails and outlook was open at the time, they are missing from webmail as well. If I have outlook closed, but have webmail open, the message is received, and opening outlook after that sends the message to outlook as well. Also I can setup her account on other machines and it works there, so it is something specific to that machine.

 

So far, I have tried creating a new profile and removing her old one, reinstalling Microsoft office, then completely removing Microsoft office and scrubbing her profile from the registry before reinstalling. Thus far nothing has worked. I'm up to the point of completely reinstalling the machine, but do to the highly personalized programs on the computer, I am hesitant to do that unless completely necessary.

 

If anyone has any ideas even what the problem actually is, I would appreciate it.



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#2 sflatechguy

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Posted 23 June 2014 - 10:59 PM

Are there any error messages in the message tracking logs on the server for that user? Are there any error messages in Event Viewer on the user's computer that might provide some clues? Do the senders get an NDR when they try to email this user? Is the user able to send mail using Outlook, or does that get stuck as well?

 

At first blush, it sounds like there's a problem with the services the Outlook client uses to contact the server and download email. Try running the connectivity analyzer tool on that particular machine: http://technet.microsoft.com/library/feba32b0-b7eb-4b1b-ba3d-99e20ba82a8c



#3 seg42

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Posted 24 June 2014 - 08:31 AM

No errors appear in the server or PC log. There are no delivery errors, because as far as the server seem concerned there were no errors. Sending email works just fine. Also, it's not all incoming emails that disappear, just some of them, although it does seem user dependent. Outlook may stop receiving mail from one user from one minute to the next (this is a literal example, I watched it happen) but mail never appears from that user again. 

 

I'll run the connection analyzer and the configuration analyzer I found late yesterday as soon as I can to see if it comes up with anything.



#4 sflatechguy

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Posted 24 June 2014 - 11:20 AM

So the email is still in the mailbox on the server, it just isn't being delivered to Outlook. And OWA works, so long as Outlook isn't open. And it only affects email from certain users, and only intermittently. Are only emails from internal senders on your domain affected, or do external emails also disappear?

This one's a head-scratcher. It's a long-shot, but make sure there aren't any incoming mail transport rules configured in that Outlook client that are interfering with mail flow. Check group policy settings for that machine as well.

Hopefully the analyzer and configuration tools will provide some clues.



#5 wpgwpg

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Posted 24 June 2014 - 11:27 AM

 I think sflatechguy is onto something with his comments about filters and rules.  It would be interesting to see what would happen with something like Thunderbird or Windows Live Mail set up to download email but leave it on the server.  That would show if the problem is within Outlook or elsewhere.  

 

Good luck.


Edited by wpgwpg, 24 June 2014 - 11:28 AM.

Everyone with a computer should back his system up to an external hard drive regularly.  :thumbsup:

#6 seg42

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Posted 24 June 2014 - 11:30 AM

I haven't had a chance to run any tools yet, but I one of the first things I did was to check the rules and filters. That one has bitten me before.

 

I know the problem has to be outlook and it has to be of that machine.



#7 sflatechguy

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Posted 24 June 2014 - 12:18 PM

You may also want to try @wpgwpg's suggestion. Set up a profile on that machine in another email client, and configure it to leave mail on the server. If the same problem occurs in the new client, it's something on the computer. If not, it's something in Outlook. I would still run the other tools as well, as those will likely help pinpoint it further.



#8 wpgwpg

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Posted 24 June 2014 - 01:04 PM

I haven't had a chance to run any tools yet, but I one of the first things I did was to check the rules and filters. That one has bitten me before.

 

I know the problem has to be outlook and it has to be of that machine.

 One other advantage of installing another email client is that this user might be able to receive all her email with it, assuming the problem IS in Outlook.


Everyone with a computer should back his system up to an external hard drive regularly.  :thumbsup:

#9 seg42

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Posted 24 June 2014 - 02:06 PM

I didn't have the chance to install another email client, and I'm fairly certain that the user would be highly resistant to using an unfamiliar client anyway, but I did setup her account on another machine. It was receiving mail fine. This says to me that the problem is specifically in her outlook, more to the point, no matter how well I think I've scrubbed the install and her profile, something is still remaining behind and is reinstituting itself upon reinstall and creation of a new profile.

 

I got a chance to run the tools over lunch.

 

I tried running the tool sflatechguy suggested, and it may be that I am misusing it, but this doesn't seem to want to work with a local exchange connection, so that was rather inconclusive.

 

However, I ran the office configuration tool, and it came up with a warning that the junk filter on  her outlook was oversized. I was aware of this fact several months ago, when it would no longer allow her to input new blocked emails. I followed Microsoft's instructions on how to increase the junk filter size, but I am wondering if this is like increasing the allowed attachment size in exchange past a certain size: You can do it but things start acting very strangely. 



#10 sflatechguy

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Posted 24 June 2014 - 02:27 PM

Another thing I considered after I posted is you may not have any other email clients on your company's list of supported/approved applications, so installing a new one may have been a no-no. In any case, the user still would have had OWA access.

 

The tool I recommended is designed to connect to local Exchange servers, so the fact that it couldn't again suggests there's a setting, group policy or registry setting on the machine that's interfering with email flow. The tool itself is pretty basic and it's hard to mess up the configuration. Does that machine have the .NET 4.5 framework installed? That might have been an issue when you installed it.

 

And as you mention attachments, do the emails that fail to download have any attachments, embedded or otherwise? Maybe check to make sure that Outlook client wasn't configured to block them.



#11 seg42

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Posted 24 June 2014 - 02:44 PM

The error the program you provided me were very strange, though. I'd send you a screen shot, but I didn't take any at the time, and I have been kicked off the user's machine so she can actually get some work done :)

 

It kept making references about a dns error when trying to connect to an automatic setting and it wouldn't accept any of the manual ones.

 

Once again I am perfectly willing to believe that the problem exists between the chair and the keyboard on this one, and evidence points to that due to the fact I forgot to check what version of the .net framework she has installed. I'm not going to get another run at this until tomorrow while she's at lunch, so I will carefully read back through the instructions and try again then.

 

One thing I am certain of, is that this isn't an attachment issue. One of the emails being blocked is her yahoo account, and the test she sent this morning was about a sentence of text, no attachments, no nothing. My mail got it, but hers didn't.



#12 sflatechguy

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Posted 24 June 2014 - 06:21 PM

Keep us posted.



#13 x64

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Posted 25 June 2014 - 01:01 AM

A couple of thoughts/suggestions:

Use exchange message tracking on a missing message - UNTICK the filer that says RECEIVE (so that you see all events for the message). You will see the progress of the email through the server. It should be delivered to the end users mailbox with a STOREDRV event.  If you see that the the message DID reach the inbox (a very useful demarcation point).

 

Run outllook.exe /cleanrules to ensure that client and server-side rules are removed

 

Consider antivirus and antispam solutions running locally in the server that integrate with Exchange (however if one of these does interfere with a message, then you will not see the STOREDRV event above).

 

For the duration of the testing, do not use caching on the users Outlook profile.

 

x64



#14 seg42

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Posted 14 July 2014 - 02:02 PM

Ok, after a lot of research and some lucky guess work, I finally found what was causing the issue.

 

The junk mail block list is only allowed so many entries, as dictated by the size limit set on the exchange server. A few months ago, the user had filled up this list, and so the size was expanded on the server.

 

It turns out, that if you fill this list past a certain size, it will start marking random email addresses as blocked, and instead of sending them to the junk folder, will just delete them. I reduced the number of blocked emails down to 500 from 9000, and suddenly everything started working again.



#15 sflatechguy

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Posted 14 July 2014 - 02:12 PM

9000 blocked email addresses? That's a lot of junk mail.

Might be time for some end-user training on how to prevent her address from ending up on spammers' lists. :rolleyes:






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