Regex Expression to replace email address domain, for users email address

Question

I am trying to solve an email domain co-existence problem with Exchange online. Basically i need it so when a message is sent to one tenant (domain.com) and forwarded to another tenant (newdomain.com) - that the To and/or CC headers are replaced with the endpoint (newdomain.com) email addresses before they are delivered to the final destination.

For Example:

1) Gmail (or any) user sends and email to sally.sue@domain.com, MX is looked up for that domain, it is delivered to the Office 365 Tenant for domain.com

2) That same office 365 tenant, is set to forward emails to sally.sue@newdomain.com (different tenant)

3) When the message arrives to sally sue at newdomain.com and she hits "Reply All" the original sender AND her (sally.sue@domain.com) are added to the To: line in the email.

The way to fix that is to use Header Replacement with Proofpoint, which as mentioned below works on a single users basis. The entire question below is me trying to get it to work using RegEx (As thats the only solution) for a large number of users.

I need to convert the following users email address:

username@domain.com to username@newdomain.com

This has to be done using ProofPoint which is a cloud hosted MTA. They have been able to provide some sort of an answer but its not working.

Proofpoint support has suggested using this:

Header Name : To
Find Value  : domain\.com$
Replace     : newdomain\.com$ or just newdomain.com 

Neither of the above work. In both cases the values are just completely ignored.

This seems to find the values:

Header Name : To
Find Value  : \b[A-Z0-9._%-]+@[A-Z0-9.-]+\.[A-Z]{2,4}\b
Replace     : $1@fake.com

But the above simply and only replaces the To: line (in the email) with the literal string: $1@fake.com

I would also need to be able to find lowercase and numbers in email addresses as well. i believe the above example only finds caps.

I need it do the following:

Header Name : To
Find Value  : \b[A-Z0-9._%-]+@[A-Z0-9.-]+\.[A-Z]{2,4}\b (find users email address, domain) 
Replace     : user.name@newdomain.com 

This is for a large number of users so there is no way to manually update or create separate rules for each user.

If i do create a individual rule, then it works as expected but as stated that requires manually typing out each user To: address And their new desired To: address.

This solution here almost worked: Regex to replace email address domains?

Answer 1

I have a couple of observations from general experience, although I have not worked with Office365 specifically.

First, a regex used for replacement usually needs to have a "capture group". This is often expressed with parentheses, as in:

match       : \b([A-Z0-9._%-]+)@domain.com$
replacement : $1@newdomain.com

The idea is that the $1 in the replacement pattern is replaced with whatever was found within the () in the matching pattern.

Note that some regex engines use a different symbol for the replacement, so it might be \1@newdomain.com or some such. Note also that some regex engines need the parentheses escaped, so the matching pattern might be something like \b\([A-Z0-9._%-]+\)@domain.com$

Second, if you want to include - inside a "character class" set (that is, inside square brackets []), then the - should be first; otherwise it's ambiguous because - is also used for a range of characters. The regex engine in question might not care, but I suggest writing your matching pattern as:

\b([-A-Z0-9._%]+)@domain.com$

This way, the first - is unambiguously itself, because there is nothing before it to indicate the start of a range.

Third, for lowercase letters, it's easiest to just expand your character class set to include them, like so:

[-A-Za-z0-9._%]