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Do player characters ever freely learn new skills/proficiencies? From what I can see, most classes get two or four proficiency skills to start, and backgrounds provide two more. Some class specializations provide a new proficiency in a tool or with a stat. But I can't seem to find anything to indicate that a PC can decide to learn a new skill that they feel suits their character's developments. Something analogous to 'cross class skills' from old editions.

In other words, if a rogue character doesn't select "Sleight of Hand" as a proficiency at first level, they'll literally never gain that proficiency.

Again, this is probably a stupid question, so if I'm missing something go easy on me. Thanks.

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    \$\begingroup\$ Does this answer your question? Is there a mechanism for gaining proficiencies or skill improvements in play? \$\endgroup\$ – ShadowRanger Apr 16 at 1:10
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    \$\begingroup\$ I don't believe this is a good dupe; despite the title, I don't think the body actually aligns with this question. The dupe is about whether 5e has any more granular representation of skill training between and beyond "proficient" and "not proficient", whereas this question is actually about how to gain new proficiencies in play. An answer that's actually helpful to this question would not fit on the dupe. \$\endgroup\$ – Carcer Apr 16 at 8:29
  • \$\begingroup\$ Agreed with @Carcer , this is a completely different question from the flagged duplicate. \$\endgroup\$ – ValhallaGH Apr 16 at 20:40
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Not Automatically

If the DM is using the Feats optional rule then the Skilled feat grants proficiency in three skills and / or tools.

Otherwise, new skill proficiencies can be gained through the optional multiclassing rules, which can grant some of the skill proficiency of the new class if going into Bard or Rogue, or as a possible non-monetary reward through Training.

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    \$\begingroup\$ @Cancer I consider it bad form to have a reference link direct people behind a paywall. At that point, a poster is advertising for the company without disclosing that fact. \$\endgroup\$ – ValhallaGH Apr 17 at 0:29
  • \$\begingroup\$ @PurpleMonkey Agreed. I think the answer does stand on its own (within the limits of not posting copyright protected material), and the links are relevant. If you have specific suggestions to improve then answer then I welcome them. \$\endgroup\$ – ValhallaGH Apr 17 at 3:51
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The game offers a few methods by which a character can gain proficiencies, aside from those chosen at first level for class and background, and any bonus proficiencies learned due to specialisation in a class.

Feats

The Skilled feat (PHB pg.170) can be chosen by characters using the optional feat rules, and simply grants the character any combination of 3 additional tool or skill proficiencies, chosen freely.

The Weapon Master feat grants the character proficiency with 4 additional simple or martial weapons (alongside a +1 to strength or dexterity) - though the option is honestly a bit weak compared to just multiclassing (see below) one level in a martial class, unless you desperately want a specific weapon proficiency and you can't afford to lose a level from your main class progression.

The feats Lightly Armored, Moderately Armored and Heavily Armored respectively grant proficiency with Light, Medium and Heavy armour.

Multiclassing

If a character multiclasses into a new class, they may pick up some new proficiencies, which might include a new skill proficiency.

When you gain your first level in a class other than your initial class, you gain only some of new class's starting proficiencies, as shown in the Multiclassing Proficiencies table.

Specifically, multiclassing into bard, ranger, or rogue allows the character to choose an extra skill proficiency from the relevant class skill list. Multiclass bards additionally learn proficiency with a musical instrument, and multiclass rogues also learn tool proficiency with Thieves' Tools.

All multiclasses bar sorcerer and wizard otherwise offer some proficiencies with weapons and armour, though notably no multiclass choice grants heavy armour proficiency by default (though if choosing cleric, several of the domains grant bonus proficiency with heavy armour as a class feature, which would still apply when multiclassing).

Prestigious training

Chapter 7 of the Dungeon Master's Guide is all about treasure and reward, and the Other Rewards section of it guides the DM in giving characters rewards for their exploits beyond simple money and magical items. Specifically, page 231 describes the offer of special training as a reward for a character, which might grant them proficiency in a skill:

A character might be offered special training in lieu of a financial reward. [...]

[...] Possible training benefits include the following:

  • The character gains proficiency in a skill.

So a DM might offer characters the chance to learn a new skill as a reward, in addition to or instead of ordinary treasure.

Non-prestigious training

If a character actually only wishes to learn a new language or tool proficiency, rather than the more valuable skill proficiency, this is given as an option when using downtime for training:

You can spend time between adventures learning a new language or training with a set of tools. Your DM might allow additional training options.

First, you must find an instructor willing to teach you. The DM determines how long it takes, and whether one or more ability checks are required.

The training lasts for 250 days and costs 1 gp per day. After you spend the requisite amount of time and money, you learn the new language or gain proficiency with the new tool.

This version of the downtime training rules requires an extremely long period of total downtime at 250 days, which probably makes it not a realistic option in many campaigns; however, Xanathar's Guide to Everything offers a reworked version in its Downtime Revisited section on page 134, which requires considerably less time:

Receiving training in a language or tool typically takes at least ten workweeks, but this time is reduced by a number of workweeks equal to the character’s Intelligence modifier (an Intelligence penalty doesn’t increase the time needed). Training costs 25 gp per workweek.

A workweek in this context is 5 days of effort, so generally about 5 times faster than the PHB version (though the cost is similar).

Honourable mention: 2nd level bards

At 2nd level, bards gain the Jack of all Trades class feature:

Starting at 2nd level, you can add half your proficiency bonus, rounded down, to any ability check you make that doesn’t already include your proficiency bonus.

This isn't full proficiency in any skills, but it does make the bard somewhat better at using any skills they aren't already proficient in, and can be had for a 2-level drop in bard. (3 levels grants Expertise in a couple of skills and 2nd level spells, which might be an attractive option for a character who has already taken 2 bard levels.)

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    \$\begingroup\$ You could mention the possibility of gaining a tool proficiency or a new language through training (a downtime activity) \$\endgroup\$ – enkryptor Apr 17 at 8:27
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A Lore Bard gets 3 new proficiencies at level 3

That's one class that gets a new proficiency as part of the class progression.

A knowledge Cleric can be proficient in any skill, temporarily

Clerics from the Knowledge Domain have a channel divinity feature that allows them to, for a short period of time, be proficient in any skill.

Most other classes don't have features that add a skill proficiency.

Feat: Skilled

If you play the game with feats, any PC can get three new skill proficiencies in place of an ASI.

Easiest way is: be a College of Lore bard.

If you want a character who can gain additional proficiencies, choose Bard, College of Lore. If you want to be able to be proficient in any skill proficiency when you need to be, play a Cleric, Knowledge domain.

If the DM provides this reward ...

Page 231 of the DMG has the option of offering a reward to a PC that includes training to achieve a new skill proficiency. This would probably be implemented during a period of down time, just as tool or language proficiency is achieved during down time (see PHB).

A character might be offered special training in lieu of a financial reward... ...Possible training benefits include the following:

The character gains proficiency in a skill. (DMG, p. 231)

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