For plex 1.15, you will have to compile the APSW binding manually. Here’s what I had to do on a raspberry pi:

1. Copy the library file to its proper place: sudo apsw.so /usr/lib/plexmediaserver/Resources/Python/lib/python2.7/lib-dynload

Restart plex, and you’re done.

Building Process

Compile a custom version of python2.7

Since Plex is running a python version that’s compiled with UCS-2, and the raspbian python is compiled with UCS-4, the apsw library that’s distributed in the repos is UCS-4, that cannot be loaded in plex.

1. Download python 2.7 from https://github.com/python/cpython/releases
2. extract it somewhere, and build it: ./configure –enable-unicode=ucs2 && make

Build python-apsw using the custom python version

1. Install libsqlite3-dev
2. Checkout https://github.com/rogerbinns/apsw/
3. Chekout the commit 64a42163b0b056d9f30cd645a581343e4052e331, which corresponds to the libsqlite version that raspbian is distributing
4. Build APSW: ~/cpython-2.7/python setup.py bdist

Source: Plex Trakt Scrobbler #521