Disguising my use of Mac Mail

Can I make the email messages I write and send in Mac Mail appear to come from my company (Windows/MS Outlook) mailbox?

With pop mail, the reply to address is shown in the recipient's mail. The reply to address doesn't have to be the sending address of an e-mail. Some mail programs a let you set the reply to address.
You could set up a another account in mail and see if it does what you want.
Mail: preferences: accounts
Click on the plus sign to create another account. The + is in the lower left-hand corner of the window. Fill in the e-mail address of your work account. The e-mail address appears to be the reply to address. Click on server setting. You need to provide a valid outgoing mail server (smtp). the server should be from your other account. It should not be your work account. It does in have to be your e-mail address you filled in above.
You may want to copy yourself with the e-mail. Click on the composing tab and check the automatic option. Pick either CC or bcc.
Robert

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