5 Replies Latest reply: Nov 6, 2010 4:15 PM by andyBall_uk
HalloweenQueen Level 1 Level 1
Suddenly after my iMac update the software on my computer, I suddenly can't attach any photos in Hotmail when I launch Safari.

I have been a Hotmail user for 10 years now and never have had this problem before. This has been my primary account for these years and I don't want to start another email account with a different carrier.

In the middle of uploading on every attachment, I get an error saying "There was a problem adding this file to the message" The files are not too large or the wrong file type.

I am using Safari 5.0.2 and Mac OS C 10.6.4

I am frustrated by this.

Can someone please help me


iMac, Mac OS X (10.6.4), using Safari 5.0.2
  • Carolyn Samit Level 10 Level 10

    From your Safari menu bar click Safari / Reset Safari. Select the top 7 buttons, click Reset. Quit Safari (Command + Q) Relaunch Safari and try attaching a photo to Hotmail.

    If that doesn't help, open a Finder window select your Home Folder in the Sidebar on the left. Then open the Library folder, then the Caches folder, then the com.apple.Safari folder.

    Move the cache.db file from the com.apple.Safari folder to the Trash. Relaunch Safari.

    If that didn't help either, quit Safari. Open a Finder window. Select your Home Folder in the Sidebar on the left. It has a small house icon. Then open the Library folder then the Preferences folder. Move the com.apple.Safari.plist file from the Preferences folder to the Desktop. Relaunch Safari. Try an attachment again. If it works, then move that .plist file to the Trash.

    Check Safari / Preferences - Security to make sure you either have: Always accept cookies or *Only from sites I visit* selected.

    You've had similar issues with Hotmail in the past. http://discussions.apple.com/message.jspa?messageID=11580566#11580566

    I don't want to start another email account with a different carrier

    At some point, you may want to consider switching to Mac Mail instead of using web based mail written by Microsoft as they may not always support the Safari browser.

  • HalloweenQueen Level 1 Level 1

    Once again, so are so prompt to respond.

    1. I tried the first suggestion, it didn't work
    2. tried the second one, but I do not have a folder called: com.apple.Safari folder
    on my computer, so I couldn't try this option, so I can't delete this file: cache.db file
    3. nor do I have a file called: com.apple.Safari.plist* file

    I looked high and low and did a spotlight search, and all of these folders/files do not exist on my new imac.

    once again, i am using os 10.6.4 and safari 5.0.2

    I still can't add attachments and get the same error message in hotmail: There was a problem adding this file to the message.

    should i trash safari and download a new version from the apple website?

    please help
  • andyBall_uk Level 7 Level 7

    paste this into a Safari address bar, or Finder-Go-Go to Folder


    and this (in Safari) will take you right to the plist
  • HalloweenQueen Level 1 Level 1

    thanks for your suggestions. i was able to paste both into my address bar, unfortunately, doing both suggestions that Carolyn mentioned previously, still has not fixed my problem.

    Should I trash Safari and download a new version?

    any other ideas??
  • andyBall_uk Level 7 Level 7

    If you remembered to restart after removing those two files - then I'd suggest testing briefly in a
    New User Account

    It's almost moments to create one & they take up almost no space, but are very useful for testing.