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The Find Familiar spell states, in part:

As an action, you can temporarily dismiss your familiar. It disappears into a pocket dimension where it awaits your summons.

The question arising from this is:

  1. Is this pocket dimension different for every familiar in the world? Thus being a personal pocket dimension?
  2. If this is true, then it should be able to store items given by its master for safe keeping away from anyone else, as long as these are items that a familiar could carry with it. Can the familiar bring small items with it into the pocket dimension for safe keeping?
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So, to your first question: The pocket dimension will be unique to your familiar.

While it's difficult to prove this, a dimension that potentially contains the familiars of every spellcaster with the Find Familiar spell in the entire universe at the same time really doesn't sound like a "pocket" dimension.

Also, what would happen if a Wizard sent his familiar to the pocket dimension at the same time as the vastly more powerful familiar of his Warlock nemesis? You have to assume that the Wizard probably wouldn't ever see his familiar again, if you see what I mean.

To your second question: RAW, the familiar probably can't take items with it.

The spell says you dismiss your familiar, not your familiar and everything they're carrying. Similarly, "it" disappears into a pocket dimension - "it" here definitely refers to your familiar, there's no reason why it would mean "your familiar and everything it is holding". It's also worth mentioning that your familiar is defined as a spirit that takes the form of an animal - so maybe it could take spirit objects with it, but probably not physical ones.

Additionally, when asked a similar question for Find Steed, Crawford said that the steed should leave gear behind. While Find Steed is different to Find Familiar, its wording with respect to this issue is similar, so the same rules probably apply.

On the other hand, Mearls says he'd allow it, but only for a few minutes. The usual caveat applies here, of course: Mearls is not a source of official rules interpretation, just a source of how he would rule things in his game. So you can pretty much take or leave his advice as you choose.

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Your first question is a classic example of the kind of thing GMs made different rulings on, back in the day, and those different rulings led to different campaign worlds. The second question is similar to the first one, but I expect most GMs will be okay with the familiar carrying a small amount of stuff (a signature hat, for example) into the pocket dimension, while some will let it carry whatever it feels like and even drop it off in the other dimension, or bring unexpected things back, and others won't let anything through at all.

If you're a player, the answer is ask your DM

If you're a DM, the answer is ask your players, by which I mean whatever makes the game world the kind of world they want to play in and you want to DM.

The "All familiars go to the universal familiar break room, which is why they sometimes show up with travel cups of brimstone-infused espresso or celestial cucumber slices on their eyes. They can take your stuff, but they'll probably pawn it by the time you call them back" answer is more Blackmoor, the "Familiars are otherworldly spirits which disincorporate into their true form when they leave the physical world. They cannot take physical objects with them, unless those physical objects are also mystically disincorporated in the proper manner, which must be researched and depends upon the specific nature of the familiar to carry the object" answer is more Greyhawk.

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    \$\begingroup\$ The last paragraph nails it. +1 :) \$\endgroup\$ – KorvinStarmast Mar 8 '18 at 20:17
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Sprites can be familiars under the Warlock's Pact of Chain (PHB. 107).

Sprites wear leather armor, carry a shortbow and longsword (MM. 283) -- since these are "part" of the sprite description and equipment, I'd venture to guess that other items it carries would be carried with it -- "it disappears, leaving behind no physical form."

I'd argue if the familiar is carrying it on their person, and isn't over encumbered, it is taken with them. That said, I can see how some DMs would rule otherwise, based only on the wording of the spell; but I think RAI, especially given the sprite, is that they take their junk with them.

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As long as you don't give your familiar a Bag of Holding or something to take with it to it's pocket dimension, I'd rule it as okay if it's a small item (the size of a tiny beast; singular item), unless you want an Astral Gate event to happen...

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I would like to throw out a different viewpoint to the accepted answer.

While I fully agree with the statement that each familiar gets its' own pocket space, as a DM I would rule that they can take CERTAIN items with them.

Familiars can attune to magic items as accepted here. If the familiar cannot take items with them, they would lose attunement after 24 hours of being dismissed. That means that the familiar could be in this constant cycle of attuning and losing attunement. And per the AL FAQ, the attunement counts against the players max attunement count, it could create a loophole.

So in my campaign, I would say non-magical, non-attuned items do not go, but attuned items do go when a familiar is dismissed.

Oh, and nothing goes with the familiar is it dies.

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    \$\begingroup\$ "It would be inconvenient otherwise" doesn't seem to logically support "therefore the rules say it can." As a DM's personal ruling to enhance convenience at their table I can see an argument for allowing that, but I can't see that meaning the rule makes such a specific, unmentioned exception. \$\endgroup\$ – SevenSidedDie Mar 8 '18 at 16:56
  • \$\begingroup\$ @SevenSidedDie, as stated by "viewpoint", "I believe" and "I would", I'm just giving my interpretation/personal ruling. My only variant is that since attuned items require a "bonding" process, they become an exception. \$\endgroup\$ – MivaScott Mar 8 '18 at 17:43
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    \$\begingroup\$ In the context of a question about what the rules are, saying what you believe (the rules are) or what your viewpoint (about what the rules are) is necessarily a statement about what the rules are. If you meant to say that you would rule otherwise, that's important to actually say. Words like “belief” and “viewpoint”, if they're not qualified with what they're beliefs about, will be read as being about the topic at hand — which is what the rules actually are. Consider revising to say “I would like to offer what I would rule as DM” or something like that. \$\endgroup\$ – SevenSidedDie Mar 8 '18 at 17:45
  • \$\begingroup\$ @SevenSidedDie, it should now be clear that this is a "point of view" answer. \$\endgroup\$ – MivaScott Mar 8 '18 at 21:50

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