I've recently migrated from a 2014 MBP to a 2018 MBP. Business as usual in terms of copying profile/emails over to the new machine. Currently running OS X 10.13.6. Everything seemed to be working fine until I attempted to send a .doc attachment. The recipient mentioned it was unreadable, asks which encoding to use. The document is essentially scrambled. I sent the same document again and had the same results. The document opens find on my machine however after sending it as an attachment I can go to to my sent box and attempt to open it and it does in fact show as unreadable. This only happens with .doc documents. All other forms of office/pdf documents send with no issues. Ive created a brand new profile and copied only the mail over and have the same results. Please advise.