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Alright, I figured one way to do this. In order for this to work you need an email account without an @gmail.com address. I used a Google Apps account, but another service provider's should be fine as well (e.g. @yahoo.com, @hotmail.com, etc.). The key is, that when you press the "Next Step" button in the "Add another email address you own", it must ask you ...

The application-password that you create will need to be added in two places in your Apple Mail app. There is your Incoming Mail Server password, which is immediately visible under your account information. Below that you can see the selection for Outgoing Mail Server (SMTP). The default will be Gmail. Click on the drop down box and select "Edit Server ...

I ran into this problem as well, and after a while determined it's related to the Keychain Access where the passwords are stored. One forum I found suggested running a "Repair" of the login keychain (available via the "First Aid" menu item), which resolved the problem for some people. For me, however, the repair process found nothing to fix. Finally, I ...

Even with SenderID and DKIM both properly configured and tested, we can't get our Stack Overflow mails through to hotmail.com email addresses -- they regularly go in the spam folder. Apparently hotmail is a tough nut to crack... The autoresponder at check-auth@verifier.port25.com is a great resource for this. Send an email to it with a valid reply address, ...

Sort of. You can create a filter that looks at the from: field and applies a specific label. You'd then need labels for each (sent-mail1, sent-mail2, etc.). The messages will still end up in "Sent Mail" as well, of course. I do something similar. I have filters to have all messages where a specific e-mail is in the from: or to: get a label for that ...

Yes. You need to add that email address as an account that you can send from (if you haven't aleady done that). Then you need to turn on the setting to reply as the account sent to. Both settings can be found under Settings | Accounts and Import. See also: http://mail.google.com/support/bin/answer.py?hl=en&ctx=mail&answer=22370

[Edited, see comments] In the Mail application you'll want to add a second (or third, etc. if you have more) SMTP account. Then, when composing an email, you can select which account from which you wish to send it. More information: http://www.macosxhints.com/article.php?story=20010401111133239

You might have a look at MSN's Sender Solutions which describes (quote) a suite of services to help senders improve their deliverability to Windows Live Hotmail consumers

Microsoft relies on various authentication filters to determine if an email is spam or not. Common industry practices include reviewing email for the presence of a SPF Validation, Sender ID and DKIM records within email received. The Sender ID Framework is an e-mail authentication technology protocol that helps address the problem of spoofing and phishing ...

On Google's support site, regarding 2-step verification, they speak directly of this issue and say this it more or less comes down to being sure that your check off the "remember this password" box Quoted directly from Google's support site: Soon after you turn on 2-step verification, you'll be alerted that your password is no longer working (see image ...

As far as I know it's just not yet possible to "delegate whole domain" on gmail. But you can do it using a IMAP client such as Thunderbird: Better multiple identity and signature management. Set up multiple "identities" in Thunderbird with email address-specific signatures, which you can't do in web-based Gmail. Hit the "Manage Identities" button in ...

There is not an explicit way of doing that, but it is a realy fantastic idea that you should sugest to the Gmail team. http://mail.google.com/support/bin/static.py?page=suggestions.cs&issue=116880&bucket=16937 I work in the same way with both emails is Outlook and you just need to get into the habit of checking the "From" address before you click ...

I think something is off with your university's mail system. I've tried sending mail using a custom From address and an incorrect password and it's been my experience that Google's mail system tells me that the remote server rejected my credentials via an error message delivered to my Gmail inbox. For example: Delivery to the following recipient failed ...