Email not going to address displayed

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Len Raphael

Senior Member
Outlook version
Outlook 2016 64 bit
Email Account
Office 365 Exchange
Outlook Office 365 local: So far only had this issue where both spouses were previously on the same contact and then later one was added to a new spouse only contact. Probably left the original joint contact alone, but not sure.

When sending emails to the spouse (second person listed originally) the send box of the email displays joint names. When clicked on, the correct spouse email address (second one listed originally) shows correct intended recipient address. Same thing afterwards when clicking on the sent mail.

The problem is that all of half a dozen emails sent to the secondary spouse email address actually went to the primary spouse email address. (Corruption seemed to exist in the portal version of Outlook, but wouldn't swear to that.) The secondary spouse doesn't use forwarding.

I had cleared all cached addresses.

Only way I could fix was deleted every contact related to the two spouses and adding them back with unique names.

If i didn't have a bunch of add-ons configured, I'd create a new profile and hope that prevents it from happening again.
Diane, three or four hours and 3 MS techs later, I was going to agree with you.

But now I'm feeling it's a wierd interaction between an add-in and autocomplete that's causing the problem.

Maybe a combo of corrupted autocomplete and an add-in.

Problem is only with contacts that have a "secondary" address (ie. home or spouse) for which I use autocomplete to select.

Sent mail shows the address I thought I had selected. Trace mail shows it went to the primary email, which in fact it did.

I could swear one of the first things I tested was disabling all add-ins, but maybe not. Because just now I disabled all add-ins, and voila mail trace showed mail went to the correct (secondary email address for that contact).

Sending via autocomplete from Outlook cloud sent correctly. Could see that in the mail trace I ran from Office 365, Admin portal.

Deleting profile on problem pc by itself did not help.

I'll try to find another guinea pig to test by enabling add-ins, one by one.

What addins do you have installed?
problem continues with other mail recipients that have more than one email address. No matter what shows before sending, always goes to primary address.

Active Add-Ins:
Acrobat PDFMaker
Microsoft Exchange
OnenNote Notes about Outlook
SendGuard for Outlook
VBOffice Category Manager
X1 Outlook RTI Addin
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