Trying Again is the 105th main story mission in Red Dead Redemption 2 (RDR2). This walkthrough will guide you through all objectives of Trying Again Main Quest including all Gold Medals for 100% completion.
Trying Again is unlocked after completing Uncle’s Bad Day.
Quest Giver: Jack Marston
Chapter: Epilogue – Part 2
Region: West Elizabeth
Gold Medal Requirements:
- Catch a fish
- Complete within 5 minutes 20 seconds
Starting Location: Beecher’s Hope, West Elizabeth
Talk to Jack
Skip the opening cinematic so you can’t see Jack roll his eyes at you when you tell him you’re taking him fishing.
- GOLD MEDAL: Complete within 5 minutes 20 seconds
You can’t call for your horse or sprint, but you can hold 
/ 
for a fast walk. Head towards the waypoint with Jack.
When you arrive, skip the second cinematic.
When you have control again, catch a fish. That’s what you’re here for after all.
- GOLD MEDAL: Catch a fish
Regardless of how small it is, make sure you keep it in order to fulfill the gold medal objective.
As soon as Jack starts worrying about Rufus, put your rod away. He will start looking for the dog, and you have to find him quickly. There is no scent to guide you, so you should just head to the southeast and when you get closer, a waypoint should pop up. Unfortunately, its a waypoint to nothing essentially.
Turn around and follow the new waypoint to Jack. When you get there, Rufus has been bitten by a snake and Jack is panicking. Skip the cinematic.
Follow the prompts to suck the venom out of the dog’s leg.
Not the time for jokes, Jack.
Once you’ve sucked all the venom out, again skip the cinematic to end the mission. (Don’t worry, the dog lives)
This finishes Trying Again main mission in Red Dead Redemption 2. Now the next quest A Really Big Bastard starts.
Next Up: A Really Big Bastard
For more Walkthroughs with all gold medals, check out the complete Red Dead Redemption 2 Story Walkthrough.
I can’t figure out if cinematics count against the time requirements for gold medals because on a couple and most notably Home Improvement for Beginners, I got the gold medal and still watched the cutscenes. The time requirement for that one is 18 seconds, so there’s no way that the cinematic counted against the gold. I also got the required finish time of 5.5 minutes on “Mrs. Sadie Adler, Widow”, and did not skip the cutscenes.