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What exactly are you having trouble with?
There should be an envelope wizard with Word that will allow you to choose a custom envelope size.
use the envelope wizard or type "envelope" in the help file, and it will walk you through step by step!
You also need to adjust the paper size (in page - setup, and perhaps also in your print options). I think your envelope is smaller than the smallest auto-option (at least smaller than the smallest in my version of Word and for my printer) so you may need to set the size by hand.
Then you just need to practice - once you have the paper size set up on your Word file, you will see a page (print view) that will look like your envelope. You can then adjust the margins to place the address where you want it to go. It may take you a couple of tries to get it just right - if you don't have envelopes to waste, cut out a piece of paper the size of the envelope and run that through the printer instead.
Remember that you may have to set the paper size twice - once in page setup and once in the print options. If you don't get both set correctly the printer may be confused.
Sometimes it's easier to make a custom sized document to match the dimensions of your envelope. This usually gives you a little more freedom with designs and spacing. Just remember that you will feed your envelopes the same direction you feed regular paper (not sideways the way you usually feed envelopes) 
Yeah, instead of going through the "envelope wizard" which was a pain in the dupah, as my polish mother would say, I just created a document in Word that was the same dimention as my envelope. I made it landscape (sideways) so that it was the actual size and orientation of the envelope and then just played with sizes and colors from that. Much easier than the stupid wizard.
thanks ladies. im gonna try nikk & jma's tips and do this biotch as a document. my envelopes are too small for the custom settings in the envelope wizard.
I have found that running envelopes through my home printer keeps jamming the printer.
Try using a print service provider to print your envelopes. For example, Mimosa Digital (http://mimosadigital.com/retail/envelope_printing.html) will print on your envelopes that you've already purchased.
Practice, lol. I have a Mac too and was using my XP side to print my envelopes. I actually had to place the envelope in the way the printer suggested and then I used the enevelope wizard in Word. It stored our reply address and I just had to type in the guest's name and address. As far as sizing, I had to place around with it. We had an A7 size envelope and I just printed on a piece of paper until the addresses where centered like I wanted them. Good luck with it
I found just getting the size setting right was the key, although I still lost a few envelopes every few would get stuck or smudge so make sure you have plenty of extras.
Within Word, there are two settings for the paper. So annoying! You have to set the paper size in both print preview and page setup (I think that's where it is anyway...i don't use Word all that often, just remember that there are two places for the setting).
Can someone clarify this a little?
I opened a Word doc, went to page setup, put in the sizes of my envelope. It's still not printing right. When I go to print preview, where exactly is the 2nd place I need to enter the sizing??
I'm trying to print envelopes that are 5.75 inches wide and 4 inches tall.
Thanks hive!
I actually did my envelopes in powerpoint. I went into page setup and made the document the same size as a number ten envelope. (Just put in your size, if it wont let you put in your exact measurements, just round it.) Then I added text boxes and a couple other details I liked.
To print them, I hit print, went into print properties and made sure it was set up to print onto #10 envelopes. It was really easy! I would try it in powerpoint. I've ALWAYS had trouble printing in word.
@kate169: OMG you saved me from losing years from my life with your advice! I was trying so hard to print multiple envelopes on my Mac, to no avail. PP took a bit of formatting, but overall it was so much easier! I was able to print 75 A7 envelopes in about 10 minutes after about 40 minutes of formatting. Thank you so much! :)
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I'm ready to kill my laptop and my printer.
I'm on a Mac. I really don't want to do 'labels' for sending out my already tardy STDC's so I'm trying to print directly on the envelope and having one hell of a time getting it right.
I'm using Word. Is there another program that is better? My envelopes are small (3.625 x 5.125)
HELP!!!