To get the "That Helped, Right?" achievement, there are a few things that can help.
Zeroth, there are two Action Packages that REQUIRE Co-op (Sorry Solo players, like myself), which can be a bit extra frustrating.
First, understand that due to Claptrap's glitchy programming, this skill may occasionally select an Action Package not relating to the current situation (and multiple Action Packages can share criteria).
So, what you get is ALWAYS basically random, though there are ways to try to help influence it, as it is based on "analyzing the environment" to choose the best ability... which can then just get replaced with any at random. You know, it IS Claptrap.
Fortunately, you can specifically respec after triggering an Action Package unlcocked from the Skill Tree, thus removing it from the list of possibilities for a wasted repeat.
There are 15 possible Action Packages, 6 of which are tied to specific Skills in your Skill Tree. To unlock all of them, you need to be a minimum of Level 25+.
I would recommend keeping track of each Action Package as it happens, as well as temporarily unlearning any tied to a Skill when they trigger.
Also, probably get the two Co-op ones done ASAP, then play solo for the rest to lock those two out of the pool of Action Packages. Make sure you have NO Skills (other than Action Skill, of course) unlocked!
-Some claim that Concordia is the prime spot to get these two done,
Now, on to the specifics:
(Default, available with the Action Skill)
Med Bot (Co-op REQUIRED) - Can trigger if your partner(s) is below 100hp or dead
Nonsensical Sacrifice (Co-op REQUIRED) - Can trigger if your partner(s) are dead
(Skill Tree unlocks)
Torgue Fiesta (Boomtrap Skilltree Tier 4, min. Lv. 15)
Pirate Ship Mode (Boomtrap Skilltree Tier 6, min. Lv. 25)
Clap-in-the-Box (I Love You Guys! Skilltree Tier 2, min. Lv. 9)
Gun Wizard (I Love You Guys! Skilltree Tier 3, min. Lv. 14)
One Shot Wonder (Fragmented Fragtrap Skilltree Tier 3, min. Lv. 14)
Laser Inferno (Fragmented Fragtrap Skilltree Tier 6, min. Lv. 25)
And here are the 16 variables (When VaultHunter.exe is activated, several are chosen, then an Action Package activates):
Enemies Present / Melee Enemy / Shot Enemy / Badass Present / Boss Present
Buddies! / Lonely Mode
Health Full / Health Low / Fight For Your Life
Shield Full / Shield Low / Shield Empty
Sadly, I don't know what each Package is tied to for triggering it, but there is some work towards that on the talk page for the skill on the wiki: https://borderlands.fandom.com/wiki/Talk:VaultHunter.EXE
(The sole exception is that the co-op ones will have the Buddies! trigger.)
Further help: Thanks to "SpectatorX" and their post I found (https://steamcommunity.com/sharedfiles/filedetails/?id=67224...
), here is a bit of control you can do for Rubber Ducky and (I assume at the moment) Med Bot and Nonsensical Sacrifice.
Step 1: Go to Concordia.
Step 2: Unequip EVERYTHING, Respec, spend a single point to unlock VaultHunter.exe
Step 3: Make sure yourself/ally(ies) are injured/FFYL (self-damage via Grenade at your feet works well)
Step 4: Stand at an edge without rails, facing outwards (to get rid of minions quickly), and activate VaultHunter.exe
(Myself, I FINALLY got Rubber Ducky on my second try this way!)