Mac Mail blocking replies to a gmail account.

I use mac mail as I have 4 email accounts (work - personal). Recently whenever I reply to an email from any, the recipiant does not receive it. It marks as sent and I have no bounce backs.
They use gmail, and receive standard emails from me fine, just not replies.
Is this a problem my end, is mac mail flagging up this particular email account as dangerous? (its not, its my girlfriends)
Or is this a problem with gmail and emails from me?
any help would be great.
Cheers
R

Consider deleting the login.keychain file and starting afresh to ensure that there is absolutely no chance that the issue is with the keychain. The login.keychain file is located in <home>/Library/Keychain
Alternatively, consider creating a new user on your Mac and then set up your email account under the new user to see if it works OK there. This will establish if the problem is related to your other account.
Chris

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