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I did find this forum thread on Spiceworks, but the issue described had no parallels with the issue I'm wrestling with and is over a year old. I have not been successful finding any record of this problem/issue being posted before (which I'm sure is not possible my own search skills are clearly at fault). To fix issue like this in Microsoft Word where the Synonyms for a particular document is in different language or the proofing language/spell check is. This suggests strongly to me that the problem is in the way Outlook handles attachments. I switched over to Apple's native MAIL app instead of Outlook and did the same thing, only to discover that the spell check works immediately (with or without using the SAVE-AS feature it appears to me MAIL allows Read/Write access to Word attachments stored in its Db). Fonts: Click Fonts in the Outlook Preferences dialog to choose default fonts for composing HTML and plain text messages. Enter the URL that you want to use, and then click OK. Highlight the word or words that you want to turn into a link. Hyperlinked text is underlined and displayed in a blue font, but you can edit the font, size, color, and style. I discovered that if I copy the text of the Word file into a new, blank Word doc, the spell check with the squiggly lines immediately works. For information on changing font sizes, see Change the font size in Outlook for Mac. When you Save As and begin editing the Word document, the squiggly red lines of the spell checker do not appear.

Open the attachment, and Word will alert you to the fact that the document before you is READ-ONLY (this, I suspect, because it remains a static part of Outlook's local mail database). Steps to Replicate: Receive an email in Outlook 2016 for Mac with a Word attachment. PROBLEM: Word 2016's SPELL CHECK (as you type) feature does not work on docs that arrive in Outlook as attachments. Products: Word 2016 (for Mac) and Outlook 2016 (for Mac) - the apps, not the browser clients.