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Travel agents that organize tours to Laos and Cambodia will know all the ins and outs , we did a mini bus trip to Laos from Surin a few years ago and the Driver spent about 15 mins signing a few papers and off we went ,in a Thai vehicle with a Thai driver Worth popping into a travel agent to get all the up to date info .I spoke to a Immigration officer at the border a while back he said its not a problem you just need to have the right paper work.The Road from Chon-Chom is not the best and even worse this time or year with the rain .
Alan, the the road from Chong Chom or Osmach is brand new two lane black top road all the way to Siem Reap.
The Phusing, (Chong Sa Ngam) crossing just inside Sisaket province is far more used friendly than Chong Chom. No touts, seemingly no customs and friendly immigration staff. Also the run in to Siem Reap is on a good road with pleasant countryside.The Cambodian visa at this border costs $25 as against further inflated prices at other border crossings.