MS Word Envelope Tool is failing

MS Word Envelope Tool is failing

When I take a normal address and select Tools > Envelope

I get some strange view where only the left few characters in the address are shown, and the envelop is the wrong orientation.

Looks normal
Looks wrong
Why?
curiouswebsterSoftware EngineerAsked:
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JohnBusiness Consultant (Owner)Commented:
At the top, it says print to Printer.
At the bottom, it says print to PDF. Can you change this to Printer?

Try resetting that and printing on a plain piece of paper (so as to not waste envelopes).

Then, it that fails, reinstall the printer driver.
curiouswebsterSoftware EngineerAuthor Commented:
That is normal, for it to offer PDF and other selections, This is a Mac version.

This is the Page Setup, so I find it odd that it shifts to some kind of landscape mode...

Page SetupScreen-Shot-2018-11-09-at-12.52.18-P.png
JohnBusiness Consultant (Owner)Commented:
Envelopes are landscape.  They go in the printer lengthwise and print landscape on the envelope.
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curiouswebsterSoftware EngineerAuthor Commented:
Yes, I know. I have used this method for years. But now, that feature started to fail. I need to know why.
JohnBusiness Consultant (Owner)Commented:
Try, as mentioned above, reinstall the Printer Driver.
curiouswebsterSoftware EngineerAuthor Commented:
Sorry, I missed that suggestion. I wonder how I do this on a Mac?
JohnBusiness Consultant (Owner)Commented:
I am not sure. You can install software on a MAC, and I think you can uninstall software as well.

http://osxdaily.com/2011/06/20/uninstall-mac-applications/
Eric FletcherCommented:
The orientation in your screen shot shows that the envelope is to be printed exactly how your printer preview displays it. Since you are specifying the “Portrait” orientation, the preview will position the envelope content as shown in your printer preview. You need to specify “Landscape”.

You note that you have been using this method "for years". When the envelope feature is invoked from a portrait-oriented letter, the created envelope will be put into its own new section “above the letter” with the orientation set automatically to landscape (i.e. just for the envelope without affecting the portrait orientation of the letter pages). Most users never notice that the envelope is set in a different section — but often run into this exact issue if (when) they try to print just the envelope or create an envelope without a letter. Envelopes are added in a landscape section
The above screen shot shows the print layout view of a dummy letter where an envelope was created by using the Mailings > Create > Envelopes dialog. I brought up the Page Setup dialog to show the margins and landscape orientation for the envelope. On the right, the Reveal Formatting pane shows the comparison of the Section width and height attributes between selections I made within the letter (“Dear Joe”) and within the envelope (“46 This Street”). As you can see, the print preview shows the text oriented the way you would want it for both envelope and letter.

If you choose to print the envelope by itself (or create an envelope with the same dimensions and section layout), you will still need to choose the landscape orientation to have it print correctly. To demonstrate this, here's what the same document looked like when I clicked “Portrait” in the Page Setup dialog.
 Same content with envelope section set as Portrait
My screen shots are from Windows Word, but will be similar to Mac Word.

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curiouswebsterSoftware EngineerAuthor Commented:
Thanks
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