So basically when two people transact on the lightning network, they create new commitment transactions for each transaction between them, these commitment transactions can be broadcast by either party back to the original blockchain at anytime in order to release funds from the lightning network back to the main blockchain.
So why can't one party just broadcast an older commitment transaction? Well it turns out they can. The way the lightning network tries to solve this, is that any commitment transaction broadcast has a three day wait period before funds are released back to the main net, which allows the party that had money stolen from them time to prove that they had a newer commitment transaction, in which case they would receive all of the funds in the channel. Basically you can not retrieve your money from the lightning network for three days, which is a horrible user experience. I suppose this is also the reason both parties need to be online at the same time to make transactions.
https://steemit.com/bitcoin/@smcaterpillar/bitcoin-2-0-the-lightning-network-explained
https://lightning.network/lightning-network-paper.pdf
Edit:
I believe a channel can close for both parties, if they both agree and broadcast the latest commitment transaction, however this still allows the possibility of one party blocking another party from spending their money for three days, or 1000 confirmations. Furthermore, if one party isn't watching, or is not online, then after 1000 confirmations one party can steal money from the other party.
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/u/adangert
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https://www.reddit.com/r/btc/comments/d1ldc8/major_problem_with_the_lightning_network_i_just/