I have had an issue two days i a row now where the bot will add me and say: inviting for task XXXX but never sends the trade request.
Yesterday it would send me a request eventually [had to try about 10+ times though (right after I told the person who wanted to trade for the item that I couldn't get it at the time) but so far this time it has not worked and even if it does start to work I shouldn't have to repeatedly try exchanging items, it is turning this site from something that saves me time to something that costs me time.

If you see 'Inviting Task XXXX' but not an actual trade request being sent, that means the bot has been disconnected from Steam but no new connection has been established.

When Steam closes the connection to the clients (our bots included) from their side, no disconnection message will be sent to the clients (at least not for the https protocol for trading) which could be used to trigger a reconnect. Simply put, the bot thinks that it is still connected to Steam but it is not. Most of the time, going into a state which could send chat message but not establishing trade (There are 3 communication protocols being used by Steam and being able to chat does not mean being able to trade). Occasionally, the bots will reconnect itself after some time but it's not guaranteed.

We could restart the botnet manually and it will usually fix the problem, but we could hardly code it into something automatic. This has been a problem since the very beginning and I don't think Steam will ever provide a solution because this is not a huge problem for normal users except for bots.

So when you think that a bot restart is needed, feel free to add me or Cara on Steam and tell us about it.