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We recently migrated one of our clients to Exchange 2013 from Google Apps, since the migration a single user has been experiencing inexplicable bounces emails and calendar updates.

Some of the bounces are generated by emails to other users inside the business, others are from messages sent to external addresses. Some emails go through one minute and not the next. All the email addresses concerned are valid and other users within the company have no problem sending to these addresses.

Each bounce message displays the email address of the recipient as a html link - the text part of the link displays correctly user@domain.com but the mailto address underlying the link is MJCEAEX-R@EX22062.lan or some variation.

The diagnostic information returned includes the following:- Generating server: S22062.EX11062.lan MJCEAEX-R@EX22062.lan Remote Server returned '550 5.1.1 RESOLVER.ADR.ExRecipNotFound; not found'

The number of bounces has slowed somewhat over time, but we're now three months from the migration and bounces continue at three to four per day.

We've done the following:-

  • Added an autodiscover record to the domain
  • Deleted the user's local machine profile and recreated it from scratch (more than once).
  • Rebuilt the user's machine from scratch
  • Tried a wide variety of local machine settings changes recommended by MS
  • Prevented Outlook from caching any email locally
  • Updated every email address in the user's address book to ensure they were in the correct format.
  • Repeatedly deleted the local machine autocomplete cache.

At this point we, the ISP and Microsoft Support are completely mystified but the problem is causing significant issues for the user.

Any help or ideas appreciated.

toomanyairmiles
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  • Could you please provide more information about your environment? How many Exchange servers there are, what are the roles, etc? – Vick Vega Oct 13 '15 at 02:20

3 Answers3

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It would seem the PrimarySMTPAddress in Exchange is going back and forth from user.name@domain.com to MJCEAEX-R@EX22062.lan. I suggest looking at your environment, and checking what values are in the proxyAddresses attribute in (I assume) Active Direectory. Also check property EmailAddresses in Exchange by the following: PS \Windows PowerShell> (get-mailbox -Identity user.name@domain.com).emailaddresses

I would imagine Microsoft Support has already gone through some of this. Have they looked at logs to see if Active Directory is attempting to change any of these attributes in Exchange?

blaughw
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Is there any chance the user is copying these addresses from a separate file? I've seen issues in the past where working email addresses were copied from a word document into Outlook and they would bounce when typing them in manually would work. The bounces would have an oddly formatted address that wasn't the address we tried to send to. Our work around was to have the users copy anything from the various documents they were using to to notepad first (so that any weird formatting was removed) and then copy the address to Outlook.

John Mello
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  • Most of the emails the user is sending are already in her contacts list, and we have sanitised the list to ensure that all addresses were in the correct format. – toomanyairmiles Oct 14 '15 at 14:37
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I take that you have identified email addresses that have this problem or does it sometimes work and sometimes not with the same email address?

I would do the following to find the route cause.

  • Take an email address with this problem then do the following.
  • Identify if this is a client or a server issue by sending an email from both the client and Outlook Web App
  • If its client side then test in both cached and online mode, version of the client maybe helpful also.
  • If it happens while on Outlook Web App then we need to look at Exchange, was the migration from Google Apps including a domain or just the emails?
Nick Eagle
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