I just got a timbuk2 messenger bag. I really like it but it kind of sucks having to dig through it everytime I lock up. Has anyone successfully sewed a strap on the outside or even under the main flap to hold a medium sized u-lock?

I'd be interested to know that as well. I have a timbuk2 as well but just use the inside pouch to hold my ulock. Oh well.

Just loop the clips on the outside of the bag around the ulock and tighten, it works, not the best solution, but it works.

i haven't had a timbuk2 in few years but isn't the outside pocket(under the main flap) sized perfectly for a u-lock? maybe not intentionally but i remember stuffing it there nicely (the back part of the pocket, where the zipper isn't)

you could always lock it to the light loop on the front of the bag....it would probably be annoying though.alternatively put it between the main strap and your chest, depending on the size of the lock.

Mine fits nicely in my back pocket.

mine too

i was going to make one, then i found this a while ago. Seagull makes them. $15 add on to msot bags (can't add on to the black bag, hense the reason i didn't buy a seagull yet. got to save up for different bag)
https://seagullbags.com/straps/

I lock mine onto the shoulder strap.

Why couldn't you sew something on there? It's yours, mod it so it works well for you.

That's probably what i'll do eventually