Wordpress Error - Image rotation is not supported by your web host
I was able to determine this was related to a missing PHP library that Wordpress uses. Perhaps the installation script in the Linode knowledgebase should be updated?
Here are the steps I took to fix it in case anyone else runs into this issue. For info on this solution I found the deails here -
I'm running Debian 8 (Jessie) also. Hope this helps!
$ apt-get update
$ sudo apt-get install php5-gd
Do you want to continue? [Y/n] Y
$ php5 -m | grep -i gd
gd
$ sudo /etc/init.d/apache2 restart
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Sometimes it is also typical to install Ghostscript, which gives additional features if you want to convert between an image format and PDF/postscript.