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What steps will reproduce the problem?
1. Start with a Warrior toon, using both ArkInventory and Outfitter.
2. With two specs, one designed for tanking and one designed for titan's grip dps, create an outfit rule that sorts your gear sets into a specific portion of your bag, depending on whether you're using your tank gear in your tank spec or your dps gear in your dps spec.
3. Switch to your spec that does not have titan's grip.
3. Reload your UI.

What is the expected output? What do you see instead?
The ArkInventory outfit rule should capture the off-hand two hander, but instead leaves it in the primary bag and does not sort it according to the rule.  The only way to avoid this is to switch to the dps spec that can equip the item, and then in addition swap back and forth between the two sets of gear.  It appears that this is caused by Outfitter 'forgetting' that the 2nd two-hander is a part of the warrior's dps outfit and you don't currently have your dps spec activated.

What version of the product are you using? On what operating system?
Outfitter 5.3.6
ArkInventory 3.02.84

Please provide any additional information below.
I haven't been able to map out the entire test matrix, but it looks like what provokes this behavior is to load the UI while you're in a spec that doesn't possess the titan's grip talent and so can't equip the 2nd two-hander.  Outfitter doesn't show the weapon as being part of the dps spec until you swap to that spec and change your gear back and forth to provoke an update, as shown by the "Used by:" option.