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My character just got a staff of the python. He has been using his familiar (owl) and a friendly pseudodragon as a little army. I'm thinking of using the snake as an ally as well--but there's no description of how much the snake can communicate with the player, if it can at all. Does anyone have any idea of guidelines for this?

From the item description:

You can use an action to speak this staff's command word and throw the staff on the ground within 10 feet of you. The staff becomes a giant constrictor snake under your control and acts on its own initiative count. By using a bonus action to speak the command word again, you return the staff to its normal form in a space formerly occupied by the snake.

On your turn, you can mentally command the snake if it is within 60 feet of you and you aren't incapacitated. You decide what action the snake takes and where it moves during its next turn, or you can issue it a general command, such as to attack your enemies or guard a location.

If the snake is reduced to 0 hit points, it dies and reverts to its staff form. The staff then shatters and is destroyed. If the snake reverts to staff form before losing all its hit points, it regains all of them.

It doesn't really mention any communication, other than issuing general commands. Can it keep watch overnight, if I tell it to wake me up if it sees any enemies? Can I have it scout ahead, as long as it's within 60 feet?

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Given that you can command the snake to guard an area, as per the description:

On your turn, you can mentally command the snake if it is within 60 feet of you and you aren't incapacitated. You decide what action the snake takes and where it moves during its next turn, or you can issue it a general command, such as to attack your enemies or guard a location.

Telling it to guard a location at night seems reasonable.

Scouting ahead seems more problematic as the snake cannot communicate back to you anything that it sees. You could always simply have it freeze or return to you if it sees something worthy of note but you'd still have no real information. Also, with an intelligence of 1 it would be up to the DM exactly how well the snake perceives more complex commands and how it even sees the world around it.

But this quote, from Speak with Animals, offers some advice on what an animal does perceive (ignore the part about 'give you information'):

...The knowledge and awareness of many beasts is limited by their intelligence, but at minimum, beasts can give you information about nearby locations and monsters, including whatever they can perceive or have perceived within the past day... (PHB p.277)

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  • \$\begingroup\$ Note that in the description it says "mentally command" \$\endgroup\$ Commented Jan 15, 2020 at 23:29
  • \$\begingroup\$ Noted... I have no idea what you infer from those two words however, except to guess that you think that implies two way communication in some way? \$\endgroup\$
    – Steve
    Commented Jan 15, 2020 at 23:37
  • \$\begingroup\$ It just shows how you give the commands to the snake and communicate to it. \$\endgroup\$ Commented Jan 15, 2020 at 23:44
  • \$\begingroup\$ When you tells it to "attack your enemies" how would it know without some sort of intelligence? Or would I sort of tell it "attack" and sort of flag all of the visible creatures that are enemies in it's head? \$\endgroup\$ Commented Jan 17, 2020 at 18:36
  • \$\begingroup\$ @AznBanjoPlaya, it has an intelligence of 1 which is still something. The rules don't go into exactly how you command it but I guess you could imagine it, at the very least, as imprinting an image of what you want it to do. Or, it's, you know, magic... \$\endgroup\$
    – Steve
    Commented Jan 17, 2020 at 21:33

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