Home Forums Mac Software Mac Applications Word on Windows-Word on macOS conflicts

I have, for some time, exchanged documents with folks who use Word on Windows, which includes editing documents originally created in Windows. Mostly it's been a reasonably smooth experience....but not lately. Two recent events were:

1. Sent a document to a friend to be translated into French. Got it back, made some changes and sent it back to the translator. He couldn't open it. I renamed the document, removing an accented letter (grave a) and he was able to open it.

2. Yesterday I received a document (different person- all English) that was created a a .doc document. I worked on it with my Word:Mac 14.7.7 and shared it with others.

However, it had a weird appearance. It's a dotted line box with a down arrow symbol inside and the description "AGM-2018-07-11-draft V2.doc 76KB". The recipients couldn't open it.

I tried changing .doc to .docx at the desktop level and sent it. However, it went with the same description as above except it said .docx instead of .doc

Note: During my editing the original document was doing very weird things. For example I'd change edited text to colour red but the entire document would turn red. Then, if I hit Command Z, the red would all go away except the section I intended to change.

Any thoughts?

Do you mean that you renamed its icon on the desktop? That doesn't actually change the format. Instead, try opening the document in Word and then go to File > Save As. Choose .docx as the file format.

Yes...renamed at desktop. Perhaps I was misled as the icon on the desktop changed to the .docx icon.


I gave that a shot but it doesn't let me make that choice. Instead I got this dialogue box:

You cannot save this document with extension “.docx” at the end of the name. The required extension is “.doc”.

You can choose to use both, so that your file name ends in “.docx.doc”.

I'm beginning to wonder if the issue has its roots in the age of the originator's software. Let's face it, Who still uses software that generates a .doc file? Microsoft introduced .docx eleven years ago.

Word has always been sensitive to font issues as it is dependent on the specific font installed on each machine for compatibility. A different version of the same font can mess up pagination and cause all sorts of formatting issues, especially in a very tightly formatted document. That is the first time I have heard of a single character causing a Word file not to open, but it is not that surprising. (When I worked in the corporate world when we sent a tightly formatted document to other parts of the company we always used PDF because the font, or at least the characters used in the document are embedded in the PDF file itself so there is no dependence on what font is installed on the local computer.)


Word documents use tags to tell its rendering engine how to format the file. The tags in Word are generally not visible. If you are curious try opening a .DOC or .DOCX file in BBEdit or TextWrangler and you will see the normally hidden tags. DOCX is a Microsoft proprietary variant of the open source Open Document. Format that uses human readable XML tags while .DOC uses non-printing binary code tags. From your description it seems likely the .DOC file you received is damaged. I would not be surprised if it had been edited many times, perhaps by many people and if you could see the binary tags and understood them you would likely be appalled at what you would see. I have been away from Word for over thirty years but I remember there used to be a "trick" related to Auto Save that was supposed to clean out all the detritus and junk then save the file. You or even better the originator of the file could run that routine and with luck the file could be salvaged.


Changing the file extension only changes the identifier that is used to determine what application is supposed to open the file. There are a lot of apps such as NeoOffice and Pages capable of opening .DOC documents. But if the internal binary tags are messed up, they may or may not be able to correctly format and display the content. If another app, say Pages, did successfully open the file, I would then save the file in Pages format then export the saved file in either .DOC or .DOCX and hopefully that might — if you are very lucky — yield a clean usable copy of the document.

Pages did open the document and immediately informed me that "This document has missing fonts" and listed 6. It gave me the opportunity to replace them them. I did, and replaced them with the same fonts that it said were missing. I was going on the assumption that Pages would pull those fonts from my library and that maybe that'd help.

I then copied and pasted into a blank .docx and did some formatting. I've since sent it back out and am waiting to hear....with fingers crossed.

My 2¢ worth:

Unless you've got a whole whack of complex formatting going on which can benefit from .docx formatting — and even if you do, it won't hurt to try and you'll find straight off whether anything changes in the formatting — open the document, go to File > Save As... and select Rich Text Format (.rtf), which does away with most formatting which you really don't need. Moreover your file/document size can shrink up to 90%!

My default Word document format is RTF, and I've never needed anything more fancy. I only use .docx or .doc format when the document comes to me from elsewhere.

In the old days (20-30 years ago), if you sent a Word document to someone who didn't have/use Word, they often couldn't open/read it. RTF allowed for anyone to be able to open/read the document. Along the way, Microsoft provided for those who didn't have Office or Word readers for same.

I'll keep my fingers crossed as well. Assuming the formatting was correct when the document was opened in Pages, you could have saved yourself some work by simply going to the Pages menu and selecting File > Export To > Word… and under Advanced Options selecting .DOCX

Yes, I got that from your original advice (thank you) but the document opened in Pages without the complex formatting on page one, so I opted to try the font replacement. I've heard from one person who says they were able to open the docx.