Finish your drink if you die, either of hull loss or crew death.
Take a celebratory drink every time you beat the Rebel Flagship, proportional to the difficlty level you beat it on.
Take another one if you died at the same time.
Take a sip every time your hull gets breached.
Take a sip every time there's a fire in your ship.
Take a sip every time a crew member dies.
Take two if you lose a crew member to an event.
Take a sip every time the Giant Spiders event shows up.
Take another if you send your crew in and they survive.
Take a sip every time you get boarded by intruders bypassing your supershield.
Take a sip every time intruders get into your cockpit.
Take two sips if you teleport crew over to an AI ship but don't have a powerful enough teleporter to beam them back alive.
Take a sip every time you encounter an enemy ship with five layers of shields.
Take a sip every time your attack misses.
Finish the bottle if you fire at least 8 projectiles at once and fail to damage the enemy at all.
Drink until you die of alcohol poisoning if you reach the Rebel Flagship and realize that you're in an Unwinnable by Design scenario due to insufficient ship equipment.
During the Flagship's Power Surges, especially its drone surge, take a sip for every time you get hit. Take two more if your shields or evasion gets destroyed. Drown your sorrows and task-kill the game executable if both get destroyed.
Take a sip every time you encounter a shieldless Auto-Scout in an asteroid field.
Take a sip every time you get into an environmental hazard such an asteroid field, ion storm, or pulsar.
Drink an entire bottle if you're playing as the Engi B ship and you die after one jump to an event that causes crew loss.
If you're using the Stealth B ship and your Glaive Beam gets knocked offline, chug for however long your beam was charging until it was disabled.
Every time you're in an event where a Slug captain offers you a drink and you take them up on the offer, take a drink to join in. If the drink was spiked and you didn't use the Rockman crew blue option, spike your own drink before you finish it.
If you're using the Slug B ship, take a sip every time you use a Healing Burst and it misses.
Take two if your boarders die as a result.
Take a sip every time an enemy ship teleports boarders and at least one of those boarders is an Engi.
Take a sip every time your door control gets disabled while you're trying to extinguish fires.
Take a sip every time an enemy Boarding Drone enters your ship.
Take a second one if it ends up in the cockpit.
Take a sip every time an enemy successfully escapes.
If you had boarders on there, take an extra sip for each one you just lost.
Take a sip every time a single missile is fired and it slips past your Defense Drone.
Take a celebratory drink if you unlock the Crystal Cruiser.
Take three sips every time you come across the "weapon just floating in space" event.