Go with your papers from the DIAN to the office from SURAMERICANA, they will sell you an insurance for 2 month (costs about 37.000,- Pesos), if you have no time or no papers go to any bigger gas station, but there they only will sell you a one year insurance (costs around 240.000,- Pesos)!
If you have the insurance you will have no hassle at all, or make your own international one on a computer what you allways can show by emergancy! :-)

In Colombia you need an insurance called SOAT , you can obtain it for 40000 pesos aproximately for one mounth. You will find store with the indication :we sell soat here.
You need to wear a jacket with the imatriculation of your bike and you must have the immatriculation of your bike on your helmet.

"You need to wear a jacket with the imatriculation of your bike and you must have the immatriculation of your bike on your helmet."

It seems that most traveller's are told they are exempt from this. I am sure this is not the case, formally, but you won't get hassled for not having it. I have a vest, but have never displayed the number on my helmet.

I chose smaller roads and didn't take any of the obvious big roads.

Never had insurance or vest.

No problems either.

Maybe just luck?

BTW. my travel health insurance covers 3party by a few million dollars, so don't call me irresponsible. I just can't get nice papers proving it.