After taking an old Exchange server out of service and creating a new one with the same email addresses, some internal email's get bounced...

Hi!

We had an old Exchange server that was having many issues.  Probably because it was on a box that was maxed out and hitting 100% usage on the hard drive and memory for quite some time.  Rather than migrate some of these issues to a new server I just decommissioned the old server and started from scratch on a new 2013 Exchange server.  I recreated the email addresses, exported and reimported mailboxes, etc.  Everything seems to be working great except some internal email get's bounced,  I've seen this before and usually just deleting the email cached address and typing them from scratch cleans it up.  However that only partially works here,  And it's hit and miss,  Sometimes it works and sometimes it get's bounced back.  And there doesn't seem to be a pattern,  Sometimes new emails work and sometimes they get bounced.

I'm thinking there must be some additional cache file that I don't know about.  Any ideas?

Thanks!
MOBlewAsked:
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arnoldCommented:
For all active users, distribution lists, that existed before still exist?  What does the mail flow trace show?

Check the AD schema there might be stale old accounts, .........

As you noted, commonly when a version is already running, one should go through the migration part.  If your new system is not adequate as soon as you get it, that would suggest it was under specd.

Adding email aging/archiving ...........

Use exchange powershell cmdlet a to list the known email address, mailboxes.

Are the same users having issues with internal emails? As senders/recipients.
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MOBlewAuthor Commented:
Thanks Arnold.

I would usually do a migration, however do to many issues with the old server it seemed better just to start fresh,

I'm not quite sure how old accounts would get into AD on a server that's never been connected.  The only thing done wad importing mail from the old mailboxes.

Wouldn't this be more on the Outlook client side?
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arnoldCommented:
The local address book could be the issue, but you stated that the bounce is intermittent, so is the email address valid and bounce, rousers sending to John smith once it goes to John.smith@domain1.com and is delivered, while the other it translates to john.smith@localdomain and bounces.

The difficulty as implied in your question is tracking down the pattern on when it bounces..
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MOBlewAuthor Commented:
Thanks Arnold.  I'm attempting to do that.  The interesting thing is when I look at the address properties of the rejected email it looks something like "firstname+20lastname2e7@mydomain.com"  Should be just firstname+20lastname@mydomain.com.

Actual firstname_lastname@mydomain.com.

I don't know where the " 2e7" is coming from.....

We only have about 10 mailboxes and 4 people are having problems, but each has a problem sending to a different person.  So finding a pattern is difficult.

Last night I deleted the address cache for one person and it seemed to work.  But this morning the issue reemerged.

Challenging issue...

I appreciate your input...
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arnoldCommented:
Check whether there is some funny character as the ending line of the email for those experiencing issues?
Shot in the dark, your email includes spaces which explains the +20 but something else might have gotten it.
Consider adding a second email address using a period instead of space. Then see whether the user's having issues might be electing the wrong recipient while typing  in .. Check the global address book at the local user address book.
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MOBlewAuthor Commented:
Hi Arnold!

Well I believe I have solved it, but this is weird!

The challenge was that people were experiencing bounced emails to others in our organization after recreating our email server.  Migration was not a good option due to corruption on the old Exchange server.  The conundrum was that there was no pattern.  One individual would have a problem sending to one or two other specific individuals, but the individuals sending and sent to were all different.  For example, person A could send to B and C but not D.  Person B could send to A and D but not C.  Person C could send to B an D but not A.

I tried deleting specific email cache address and the entire cache list.  This did not help.  I went through the process of recreating the GAB and recreating each address, but this also did not help.

There were no problems with addressing using OWA.

This is what finally worked.  I realized that, even after deleting the cached entries, that outlook was still matching addresses from the persons contact list.  I believe these contact lists were initially created using the GAB.  But the users have since added notes, etc so I did not want to delete the contacts.  So what I did was deleted the company email address within the contact.  (This was a shot in the dark but I was at a point where I would try anything).  The address was then repopulated by the GAB.  That seemed to do the trick.  We have not experienced any additional bounce backs since then.

I appreciate all of your input.  I hope this will save someone else some hair.
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MOBlewAuthor Commented:
It was my own solution but it is a bit unorthodox.  it did work for me but I'm not sure it's relicatable.
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