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How do I setup my SquirrelMail to have multiple from addresses

I'd like to sometimes send email from one address, and other times use a different from address.

One of the links on every page of your Squirrelmail account is a link to manage your "options" -- under "options" you should see a "Personal Information" option. Under "Personal Information" options, there is a section for "multiple identities" -- this is what you are looking for. Click the "Edit Advanced Identities" link -- from there it should be pretty straightforward.