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Let's say I take 10 levels of Bard and then 10 levels of Rogue.

This would give me the following skill proficiencies:

  • 2 from my background
  • 3 from Bard level 1
  • 1 from Rogue level 1

This is a total of 6 skill proficiencies, and with Bard level 3 and level 10, and Rogue level 1 and level 6, I would have 8 skills to put Expertise into. I can put one of these Expertises into Thieves' Tools, but there is still one Expertise left to be used.

Is this Expertise simply lost? Must I take one of the skill feats if I want to be able to use this Expertise?

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  • \$\begingroup\$ There could be more tool proficiencies from background as well, or am I missing something? I was missing something, expertise can't be used in tool proficiencies. My bad. \$\endgroup\$ – HellSaint Apr 16 '18 at 23:53
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    \$\begingroup\$ What problem are you trying to solve in the game that you are playing? What level is your character now? How many levels has your group agreed that this game will last? \$\endgroup\$ – KorvinStarmast Apr 17 '18 at 0:37
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Yes, the way you did it, you just lose this expertise.

Okay, let's start with some background.

Do expertise bonus stack?

It seems they don't. But what doesn't stack is their bonus.

BUT...

RAW, it seems you can put your expertise twice in the same skill. It just won't stack the bonus (therefore there is no reason to do it). Let's check why I say we can do it:

From Rogue

At 1st level, choose two of your skill proficiencies, or one of your skill proficiencies and your proficiency with thieves’ tools. Your proficiency bonus is doubled for any ability check you make that uses either of the chosen proficiencies.

At 6th level, you can choose two more of your proficiencies (in skills or with thieves’ tools) to gain this benefit.

From Bard

At 3rd level, choose two of your skill proficiencies. Your proficiency bonus is doubled for any ability check you make that uses either of the chosen proficiencies.

At 10th level, you can choose another two skill proficiencies to gain this benefit.

Note that in the 1st Rogue level and 3rd Bard level, there is no "another" or "more" or "other" skills. Obviously, because so far they aren't considering Multiclassing (as it is a specific rule). You would expect to see some clarification about this in the Multiclassing section, but there is none.

RAW, you can get expertise twice in the same Skill, but it does not stack.

So yes, you just "lose" this expertise.

Quick Remark about the Multiclassing you did

Note that if you go the other way around multiclassing, starting with rogue, you will have 7 skill proficiencies (4 from rogue + 1 from bard + 2 from BG) and a thieves' tools, so you can actually use all your expertises.

Other solutions

A great comment added by Giuseppe added some more solutions:

  • You can take a race that grants a skill proficiency, such as elves.
  • As you mentioned in your question, you can get a feat that grants a skill proficiency, such as Skilled.
  • Instead of taking 10 levels in Rogue, since you get the max expertise at 6th level, you could instead multiclass into Ranger, which would give you an extra Skill Proficiency. Side Note: By PHB Ranger is the only class that you could still get more Skill Profs.

TL;DR:

RAW, you lose 1 point of expertise. RAI, you probably lose 1 point of expertise. But you can still build your skill monkey by starting your multiclassing with Rogue instead of Bard. Or you can just talk to your DM.

Side note: Fun concept you got there to get to this question.

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    \$\begingroup\$ Other options that can solve the problem include: being a race that grants a skill proficiency, such as elves; choosing a feat that grants a skill proficiency, such as skilled; multiclassing a third time into a class that grants another skill proficiency, such as a ranger. \$\endgroup\$ – Ruse Apr 17 '18 at 16:33
  • \$\begingroup\$ @Giuseppe added that to the answer. Nice ones. \$\endgroup\$ – HellSaint Apr 17 '18 at 21:30
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    \$\begingroup\$ It may be worth mentioning that the type of Bard matters as well - a Lore Bard gets three more proficiencies at L3. That's usually part of the prescription for a skill monkey. \$\endgroup\$ – T.J.L. Apr 18 '18 at 12:52

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