Problem solved. The last error posted after trying with Safari gave me a clue what was wrong, since the original errors gave me nothing to go on. The issue is not Serendipity at all, it's with the Hiawatha web server. By default it has a very small, IMO, amount of data that can be sent in a request....

Hmm interesting. Problem still exists with chrome and firefox, so on your last suggestion I fired up Safari on my MBP and Hiawatha the web server spits out a "413 - Request entity too large". The size of the image I am trying to upload is: # ls -la IMG.jpg -rw-r--r-- 1 cwatson geneology 34...

The error is:

Error 101 (net::ERR_CONNECTION_RESET): The connection was reset.

Same error before and after changing the upload dir to 777. :/

No, I am not. I just checked the first 5 of 42 images that I am trying to upload and the largest was 335K.
Is that a hard limit 2MB? Thats good to know for the future.

# php -i phpinfo() PHP Version => 5.3.9 System => FreeBSD 9.0-RELEASE FreeBSD 9.0-RELEASE #0: Tue Jan 3 07:46:30 UTC 2012 root@farrell.cse.buffalo.edu:/usr/obj/usr/src/sys/GENERIC amd64 Build Date => Jan 19 2012 17:33:09 Configure Command => './configure' '--with-layout=GNU' '--localstatedir=/var' '...

As the subject says I just installed Serendipity and for the most part it works fine. But I just tried to upload some photos to the media db using the admin panel and when i try and upload multiple images or one image at time it immediately comes back with a connection reset error. I am certain it i...