Later it shrunk the file some, but only by about 100 mb
That's because your file is still full. When you truncated the file there wasn't much information it could get rid of. Then when you shrunk the file you didn't see much change because there wasn't much spare space to get rid of.

In my previous post I wrote "you need to investigate why the log file is growing so large in the first place". The reason I wrote that was because it was important. It was so important, in fact, that I'm going to write it again with a few exclamation marks: you need to investigate why the log file is growing so large in the first place!!!

Carry out the following steps, in order:-
1. Take a full back up.
2. Truncate the log
3. Shrink the long

At this point the files will probably get significantly smaller. Then, as an added step to make sure you don't get into this state again:-
4. Look at the recovery mode on the database. It's almost certainly set to full. Change it to simple.




As for the timeouts, I have no idea, and anything anyone else posts at this stage is a guess at best because there could be a million different reasons and it might not be connected to shrinking the file. You need to do some investigation yourself first:-

1. Check which queries are timing out. If it's the same query all the time then you should examine those queries individually and performance tune them.
2. If it's all different queries then you've probably got a systemic problem. Disk IO is the biggest bottlenek so ask your provider if they've got any tools you can use to analyse this.

I very much doubt that the log file re-growing is the cause of your time outs. It would introduce a delay once at the moment it grew and then it would go back to behaving normally. It wouldn't give you the continuous timeouts you're describing.