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I'm using apache 2.2 + ssl + wordpress. I can easily upload files up to 1GB without using SSL, but when I enable SSL I can only upload files up to ~250 MB. Error logs shows nothing.

Am I missing somekind of SSL config?

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Take a look here, one of these should solve your problem, https://stackoverflow.com/questions/8896644/request-entity-too-large

Most likely you need to change the SSL buffer size in your apache config file.

SSLRenegBufferSize 10486000

The name and location of the conf file is different depending on distributions.

In Debian you find the conf file here, /etc/apache2/sites-available/default-ssl.conf

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