What happens when you attempt to upload an image file - time out, error message, error logged in the event viewer, etc.?

How large (KB or MB) are the image files you are attempting to upload?

Are the JPG images standard jpg's or a "lossless" variation that may not be able to be processed by .Net GDI+ methods?

Please post the element from web.config.

Please provide more details and post complete error message including stack trace from event viewer if possible.

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Bill, WESNet Designs
Team Lead - DotNetNuke Gallery Module Project (Not Actively Being Developed)
Extensions Forge Projects . . .
Current: UserExport, ContentDeJour, ePrayer, DNN NewsTicker, By Invitation
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Try adding the following attribute and value to the <httpRuntime> element:

requestLengthDiskThreshold="8192"

That is the default value for DotNetNuke sites. Without the requestLengthDiskThreshold element the default ASP.Net value is only 256 bytes. Some modules which handle their own file upload don't properly buffer the upload file stream if  the requestLengthDiskThreshold is set to too low a value. I've also seen one module (can't recall which one) that would not handle large uploads if the requestLengthDiskThreshold was set to any value other than the value for maxRequestLength. Note also that the requestLengthDiskThreshold must not be set to a value larger than that for maxRequestLength. Although not the cause of this issue I would also reduce executionTimeout as it now allows for 60 minutes. One site of mine routinely does uploads in the 12 MB range and as I recall we are using an executionTimeout ="300".

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Bill, WESNet Designs
Team Lead - DotNetNuke Gallery Module Project (Not Actively Being Developed)
Extensions Forge Projects . . .
Current: UserExport, ContentDeJour, ePrayer, DNN NewsTicker, By Invitation
Coming Soon: FRBO-For Rent By Owner