Mail: REPLY always goes to an old address...

Okay Gurus...
A friend of mine, John, just changed his email address. His old address was (let's say) a hotmail.com address. His new address is a gmail.com address.
Now, whenever I recieve and email from [email protected], and I hit "reply," the reply-to address is always his old hotmail address. Every single time. It comes in from gmail, but as soon as I hit reply, the address in the reply to is always the old, dead address.
I have tried (multiple times) removing the old address using the "remove from previous recipeints list" in the reply-to field, and I've removed it from the actual list through the Window menu. However, whenever I get an email from him, the reply to still calls up the old address. I've checked his contact info in my address book and only the new email is listed - I removed the old one.
This also happens on my iPhone, if I hit reply to the new gmail account, it still puts the old hotmail.com address in the reply-to slot. Same with the iPad.
This is drivin me nuts. I know, that sometimes in haste I don't catch this, and he's never received emails that have gone to the old address.
What's the fix here? I've done the obvoiusly prescribed things, but it's still not working. Please help.

Anybody? This has been driving me nuts...

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Hi Mike,
I had the same issue and managed to solve it.
Go into Mail>Preferences>Accounts
Then in the account information tab, at the bottom should be outgoing mail server (SMTP) and click the drop down box
Mine had a few different servers in it so i went into edit SMPT server list. Click advanced and it will tell you which ones are going from which email address.
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Hello all
I just moved to MAIL after 12 years of Eudora.
I’m MAIL 2.1.3 in Mac OS 10.4.11 PPC.
my problem
People send emails to me at 2 different email addresses. Both of them are stored on two different servers, and thus two different POP setups. Let us call them Eunice.net and Poppy.net
I have MAIL setup to pull my emails off both different servers. I think it would be best to always send emails from one particular email address, ([email protected]) using the one particular email POP server. (Eunice.net)
My problem is that when I get an email sent to me at Poppy.net, want to hit reply and have it go out by way of the Eunice.net SMPT (POP) server (and with the return address as [email protected]
The problem is that I can’t find a way to configure my Preferences/Accounts to make this happen. As of now, I hit reply to an email sent to [email protected]… and it tries to send the email out via Poppy.net (and fails) - i get an error messsage.
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Mail, Preferences, Composing, Send New Mail from is indeed set properly - so this is why i'm baffled.
Note that this setting is "Send New Mail from", in other words, when you create a New message, not Reply to an existing message. When you create a new message, does it do send from the specified account? Note that this will only work if no message is selected, else it will create the new message using the account of the selected email (assuming Mail can figure out the account from the header).
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*+How is the "From" address determined in a new message or a reply?+*
+Mail will try to determine the correct "From" address to use when you compose a new message or reply to a message.+
*+When you compose a new message, the From address is selected in the following order:+*
+If a message is currently selected, Mail uses the account the message belongs to, if it can be determined from the headers of the message, or by the IMAP mailbox the message resides in.+
+If an IMAP mailbox is currently selected, Mail uses the account the IMAP mailbox belongs to.+
+If no message or mailbox is selected, Mail uses the email address for the first account listed in the Accounts pane of Mail Preferences.+
*+When you reply to a message, the From address is selected in the following order:+*
+The To and Cc fields are compared to email addresses you have set up in Mail Preferences. Mail uses the first matching address it finds as the reply address.+
+If the message is in an IMAP mailbox, Mail uses the email address for the account the mailbox belongs to.+
+If all else fails, Mail uses the email address for the first account listed in the Accounts pane of Mail Preferences.+
One way to ensure that the messages are sent using the Eunice.net SMPT (POP) server is to set that server as the SMTP server in your Poppy mail account (putting your Eunice settings in the SMTP server settings dialog). That won't address the ReplyTo issue (although you can set that manually in the ReplyTo field, accessed via the button next to the subject line).
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Begin forwarded message:
From: Frances Topping <[email protected]>
Subject: Re: - Old computer I had is OSX Snow Leopard with Entourage. New one is OSX Mavericks. Using Mail where are my addresses and old address book. Transferred old computer backup by Time Machine and other things work? Can't see a symbol for address book.
Date: August 25, 2014 at 9:46:01 AM EDT
To: discussions-replies <[email protected]>
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Mail: REPLY always goes to an old address...

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