Does Microsoft Word 365 regularly detect words that you commonly use as misspelled words?

you could change this by adding custom words to the dictionary.

FAQ

Why is my Add to Dictionary option grayed out?

MS Word Header

This seems like a bug in the software.

Try going toFile > Options > Proofing > Custom Dictionaries.

Then select theDictionary language.Then remove the checkbox next to the dictionary item, then check it again.

Add to Word dictionary

These steps seem to toggle something in the software that makes the Add to Dictionary option available again.

Why doesnt Word seem to be spell-checking correctly?

Check to check that you are using a valid dictionary file.

Word 2016 More Comments option

you could do this by going underProofing > Edit Word Dictionaries… > Edit Word List…

Word 2016 Custome Dictionaries button

Word 2016 Edit Word List button

Word 2016 Add word to dictionary

Word 2016 More Comments option

Word 2016 Custome Dictionaries button

Word 2016 Edit Word List button

Word 2016 Add word to dictionary