Trying to spectate a friend's match sometimes just doesn't work

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Usually spectating friends works flawless but for some reason some specific people on my friends list just have games which cannot be spectated. Clicking spectate game brings up the usual connecting to match text but never gets into a match, the console spams the same retrying sync message error 404. Going to the url in the console usually just gives me the message "broadcast has not yet started".

Another note is that on steam, it says this friend has been in the match for X amount of time but in game it never updates and only stays at whatever time it was whenever I opened the game.