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Valid for Sitecore 5.2, 5.3
Size Limitations for File Uploading

Q:

Is there a limit of file size when uploading a file into Media library?

A:

At runtime, the .Net framework checks the maximum size for the requested object. This information is obtained from the application's configuration file. If the limit is not specified in the web.config file, then it will be obtained from the machine.config file. If you want to allow a user to upload with a greater size, be sure to change the 'maxRequestLength' value.

You can set it to the appropriate value to satisfy your needs.

For example:

<!-- set to 128 Mb-->

<httpRuntime maxRequestLength="128000" />