She was printing it to a local printer via the
terminal server, which seems to have a problem
with chosing envelopes (no matter the setting) and
would not even print it as landscape (it would
print, but wouldn't flip the data at all to be
landscape).

I was able to install the converter pack for .docx
docs on her local machine though, so she was able
to open the document there and print locally fine.

She is logged in under the remote desktop.

She has printed envelopes before on that printer 
with no problem. This time, when she goes to try 
to print, it just takes the envelope but nothing 
gets printed on it.

Word Document file she is priting.

She is available all day. She needs to do the 
mail route so would like to have someone come 
over asap.