machine smtp.gmail.com login personal@example.com port 587 password fakepassword
machine smtp.gmail.com login work@example.com port 587 password fakepassword

(setq mu4e-get-mail-command "offlineimap")
(setq mail-user-agent 'mu4e-user-agent)
(setq message-send-mail-function 'smtpmail-send-it)

(setq smtpmail-stream-type 'starttls)
(setq smtpmail-default-smtp-server "smtp.gmail.com")
(setq smtpmail-smtp-server "smtp.gmail.com")
(setq smtpmail-smtp-service 587)

(setq mu4e-contexts
      `( ,(make-mu4e-context
           :name "personal"
           :enter-func (lambda () (mu4e-message "Switch to Personal context"))
           ;; leave-func not defined
           :match-func (lambda (msg)
                         (when msg
                           (mu4e-message-contact-field-matches msg :to "personal@example.com")))
           :vars '(  (user-mail-address . "personal@example.com"  )
                     (mu4e-drafts-folder . "/personal/drafts")
                     (mu4e-sent-folder   . "/personal/sent")
                     (mu4e-trash-folder  . "/personal/bin")
                     (mu4e-maildir-shortcuts . (("/personal/INBOX" . ?i)
                                                ("/personal/sent"  . ?s)
                                                ("/personal/bin"   . ?t)))
                     (smtpmail-mail-address . "personal@example.com")
                     (user-full-name    . "Matt Valentine-House" )))
         ,(make-mu4e-context
           :name "work"
           :enter-func (lambda () (mu4e-message "Switch to Work context"))
           ;; leave-fun not defined
           :match-func (lambda (msg)
                         (when msg
                           (mu4e-message-contact-field-matches msg :to "work@example.com")))
           :vars '(  (user-mail-address . "work@example.com" )
                     (mu4e-drafts-folder . "/work/drafts")
                     (mu4e-sent-folder   . "/work/sent")
                     (mu4e-trash-folder  . "/work/bin")
                     (mu4e-maildir-shortcuts . (("/work/INBOX" . ?i)
                                                ("/work/sent"  . ?s)
                                                ("/work/bin"   . ?t)))
                     (smtpmail-mail-address . "work@example.com")
                     ( user-full-name    . "Matthew Valentine-House" )))))

(smtpmail-smtp-user . "me@gmail.com")

(smtpmail-smtp-user . "me@work.com")