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Google Apps for Business

An employee, "Bob", has left the company but we are not ready to delete his account (bob@ourcompany.com) yet. Now "Bob" is at another company we work with and one of our users keeps mistakenly emailing bob@ourcompany.com instead of bob@theircompany.com.

How to prevent our other users from emailing "Bob" at his old email address?

I thought of using default routing or content compliance to re-route email to his new account, but this wouldn't work because then confidential information might get to him.

Ideally, there would be some way to tell Gmail that any of our users trying to email bob@ourcompany should be emailing bob@theircompany.

Is there some way to do that?

I.e. "did you mean to send this to ..."

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Your company should not be trying to automate the process, specially not for An employee and one of our users. There may well be people for whom "Bob" was their contact at your company who do not become aware of "Bob's" change of employer until long after that happened. So even if specifically addressed to "Bob" they may be attempting to communicate with your company. (In other words, there seems no guarantee that all the mail sent to "Bob" at bob@ourcompany.com is personal.)

So not only do you need to ensure you are not leaking confidential information (in what you send out) but also that you are not missing important information that is being sent to your company (in "Bob"'s name).

For that who from or who to or even both is not sufficient for a judgement. Somebody is going to have to read the body of such e-mails and decide the appropriate treatment on a case by case basis - at least until enough of "Bob"'s contacts have been made aware of his change in employment.

Those that appear intended for bob@theircompany.com should be returned to sender, possibly with a canned message or something more ad hoc that explains "Bob" is no longer employed by ourcompany.

Those that appear intended for ourcompany should be passed over to a suitable colleague of yours. (And that colleague be made responsible for notifying the sender of "Bob"'s departure.)

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