My Wordpress upgrades have always gone smoothly. Maybe it’s because I rarely download and use plugins. Maybe it’s because I almost know what i am doing. Maybe it’s because Wordpress rocks. Who knows? Anyway, the fact that everything has always gone so smoothly has led to me slowly developing bad habits like (stupid, I know) not backing up anything before I upgrade. Anyway, upgrading to Wordpress 2.5 did not go smooth and I will never upgrade without backing everything up again!!

Everything looked great at first but then I went to upload an image and everything went kaput. No image, nothing, nada, zilch. The fancy new flash based media uploader wasn’t going to let me upload anything. Now, maybe it’s just me, but isn’t uploading media sort of important? Wordpress isn’t that complicated, and really isn’t that involved. Besides uploading media and writing posts/pages was else is there? Why would such a major problem be overlooked? Apparently, even though I’m seeing lots of posts about people having problems the development team at Wordpress never encountered them.

Here is the sticky with some possible solutions

At first I tried option 3 (Update your Adobe Flash to the latest version) but that did not change anything. Then I tried option 1 (Make sure you uploaded all the WordPress files correctly). Usually I delete everything except the wp-content folder, wp-config and my .htaccess file. This time I went a step further. First I backed up all the files on my server, then I deleted everything leaving me with an empty folder. Next I copied all the Wordpress 2.5.1 files to the server. Then I copied my wp-config and .htaccess files file from my backup. I reverted to the default theme and tested uploading an image. Bingo. It worked. *WHEW* All I had to do next was copy over content from my backed up themes, plugins and uploads folders and I was back in business.

So, before you start playing with permissions and playing with mod_security, just try a completely fresh install. Obviously make sure you have a backup. You’ll thank yourself later.

**UPDATE**

Well, even though I thought the clean install had fixed my problems, I was wrong. The problems returned a few days later. Luckily the latest version of Wordpress 2.6.2 appears to be running OK so, if you are still having problems uploading media, try 2.6.2. It works for me!