Help? Can't email or upload image files - other files ok

I'm working on my friend's computer and can't seem to solve this issue.

He can no longer upload pictures or images. He used to be able to attach photos in email but no longer can.
I even tried to upload a small photo (137kb) to drop.io with no success.

I tested PDFs and word docs. Both attach in email and upload to drop.io just fine. But images won't attach or upload. I've tried both jpgs and gifs in two different file sizes.

The test file at 137kb hangs when attaching to email and when uploading to drop.io. However the 3kb test file will attach and upload so image files are not being blocked completely.

A 2MB PDF attaches in email and uploads without any problem.

I thought it may be a Norton conflict so I uninstalled Norton.
Didn't fix the problem.

Computer: Sony Vaio VGNAR190G Laptop, 2GHz, 1GB RAM
OS: XP MCE SP3
Connection: AT&T 3G Laptop Connect USB Adapter

Any help would be appreciated.

 

hi, are you using outlook, outllook express, or a web based email like hotmail?

 

not using outlook or outlook express.
I've been trying to attach in yahoo and my friend as also had no success using another web based email.

I'm pretty sure it's not Yahoo specific because the image file wouldn't load to a brand new drop.io account either.
Larger PDFs and word docs attach fine.

Any ideas?

More detail:
-browser doesn't matter. problem exists in both IE6 and FF3
-i can't upload a zip file with a photo in it

 

Additional Info:
-files under 60kb will load. files over 60kb will not attach or upload anywhere

 

Nobody?

Ok... after messing around with it more, I'll post my own theory for anyone who may be experiencing the same issue.

Since PDFs could be uploaded with no problem, I decided to take a wallpaper picture that came with the system (a 400kb file), change the extension from jpg to pdf and try uploading it.
It worked, wheras, the photos I was trying to upload didn't work.
So then I thought, perhaps it's something with the way the jpg is compressed (I really don't know if there are different ways, - e.g., phone pic vs. camera pic - but I reacall reading somewhere that it was possibly a problem for someone else). So I tried taking the same wallpaper, changing the extension back to jpg and uploaded it.
It worked.
Weird.

So then I started trying other jpgs (including the ones I had problems with for the past few days, plus a new 3MB photo) and they all were working now.
Curious.

The only difference between the now successfull attempts and previous failed attemps was the time I was trying to upload.
The successfull uploads were done at 12:30am.

So, here's what I figure...
The AT&T 3G laptop card may be restricting jpg (and perhaps other files) most of the day (or during peak times). It certainly can't be that the system/network was just too busy (during the 3 different days I tried during the morning/afternoon/evening hours) because the other, much larger files always uploaded without a problem no matter what time of day.

Now, this is just a theory, but it's the only reason I can think of since larger PDFs and word docs would upload during the day, but not jpgs.

Hope this helps someone somewhere someday.