I just uploaded my transcripts and I had no problem. Are you sure your files are under the size limit?

Also, did you send in your physical stuff yet? I'm kinda confused cause the website states to send a portfolio, department application, and a printed copy of the Application for Graduate Study. But the online application states that you only need to send in your portfolio and department application 

When I tried uploading on Firefox it would not work, but on Safari it was not an issue.

I was confused about the physical stuff too. I sent in my portfolio along with hard copies of my Application for Graduate Study and essay. Hope that was the correct thing to do. I might call their office later this week just to make sure.

I called spoke with grad advisor, she said to mail in portfolio, dept app, and graduate admissions app only

fuck it man, I just sent them everything (portfolio, dept app, graduate admission app, transcripts, essay). That's what the dept app said. 

yea i saw that too on the bottom of the dept app, better safe than sorry i guess

just to backup Cizz, here's the email I got from UW:

Apologies for the conflicting information.  This is the first year we have moved to a mostly online application and we missed updating some references on our documents.
The information on our department website is the correct one:

A portfolio of work in graphics and design (or similar work appropriate to the program). The portfolio should be no more than 20 pages (sheets) in a format no larger than 1.5 x 10.5 x 11.5 inches. It must show evidence of the applicant's preparation for study in architecture. For the two-year program this should include models and freehand, technical, and digital drawings of architectural projects. If possible it should also include other examples of design and artistic work, such as furniture, painting, and/or photography. (Advice on preparing the portfolio)
A printed copy of the Application for Graduate Study. – this is the online UW Graduate School application that you have been uploading information to.  Once you complete and pay the application fee, you will be able to print a copy of the application (which summarizes the data onto one sheet).
A printed copy of Department/Program Application.

Already sent in my application thou lol