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Outlook Error After Changing SMTP/Email Address - Exchange 2010/Outlook 2010

Hello experts,

We are in the process of cleaning up SMTP/email addresses (ie, removed invalid characters from the email address) from distribution groups/distribution lists and after doing so, users are reporting the "email message cannot be delivered to <email address> because the email address is no longer valid" message once they are using outlook. BTW, only the SMTP address changed (alias and display name remained unchanged) They are getting the emails but the message is causing confusion.

We have Exchange 2010, Outlook 2010, cached mode is enabled.
I haven't tried disabling and enabling cached mode because it is grayed out for me but ran /cleanautocompletecache, and no avail.
Checked adsiedit property - proxy attribute and mail have the same values (which = new updated email)

Any suggestions?

Thanks!
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Bartender_1
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@Christopher thank you for the note. I will try that. I actually wanted to avoid to add the 'old' email address as an alias because we are about to turn on directory sync for O365...
What are the concerns with directory sync for O365?
Will this be a hybrid exchange setup?
Are the old addresses using a different domain? Or is it just a preference to not use aliases?

I haven't had any difficulties using aliases in our hybrid environment.

Christopher.
@Christopher:
What are the concerns with directory sync for O365? our SMTP addresses either have "!" or "&" in them.
Will this be a hybrid exchange setup? Yes it will be a hybrid setup
Are the old addresses using a different domain? No same domain Or is it just a preference to not use aliases? just a preference not to use email aliases with invalid characters.
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Hi,

what happends if you delete that email address from Outlook Autocomplete, and then select it from Address Book?
When user start typing address, they get an autocomplete list of all addresses, and you should delete it from there. Try on one user and let us know if email will go.

Regards,
Ivan.