Spymaster

You have a number of trained spies equal to your proficiency bonus (use rules for sidekicks). The level of each spy is equal to half your level, rounded up. These spies are loyal to you and can attempt to infiltrate positions of import and report back their findings. 

Standing

Your spies have various ranks within their position, known as Standing. When a spy first infiltrates a position, they begin as a New Recruit, and will begin completing orders and seeking to increase their Standing. Their Standing reflects how your spy is viewed by those that surround them, not necessarily actual ranks within an organization. Their Standing will modify any skill checks pertaining to their orders in the following ways.

1. New Recruit: -10 to checks

2. Novice: -5 to checks.

3. Adept: no modifier to checks

4. Ally: +5 to checks

5. Trusted Confidant: +10 to checks

Issuing Orders

When you complete a long rest, you can issue one of the following orders to any of your spies. If you do not issue any orders, they will Maintain Cover. You cannot issue them a new order until you receive the results of their last order. If you do not have magical ways of contacting your spies (animal messenger, sending, etc.), you can communicate with them using coded letters that travel via courier, taking 1 day to reach them for every 25 miles that separates you.

The following options have recommended skill checks to complete the order, as well as typical time frames to complete the order once it is received. Your DM may ask for different or additional skill checks as needed, such as Athletics in order to promote in an army.

• Maintain Cover: Your spy will continue in their current position and maintain their cover (Deception with Advantage). They will not attempt to discover any intel, though they may still contact you to notify you of notable events, such as a king preparing his army to march to war.
• Promote: 1d4-1 days per current rank. Your spy will perform admirably (Performance) in their current position, attempting to move up the ranks so they can get closer to more influential individuals. Note: Your spy has advantage on the check if their class is naturally suited to the position; Warriors are best at infiltrating military organizations and monasteries, Spellcasters are best at infiltrating groups of mages and cults, and Experts are best at infiltrating royal courts and underground guilds.
• Gather Intel: 1d12 hours. Your spy will attempt to uncover (Perception or Investigation) unsavory secrets about a person in power, this may also include mechanical details such as creature type and vulnerabilities.  Note: You can order your spy to investigate a specific piece of information, adding 1d4 days to the order.
• Influence: 1d10 days. Your spy will attempt to influence an individual in power. This influence can be advice (Persuasion), a threat (Intimidation), or a lie (Deception). The result of the influence can be a promotion, payment, intel, forming an alliance, or helping to implement a policy that benefits you. Note: If you know a secret about the person, you can blackmail them, granting advantage on the check.
• Retrieve: 1d12 hours. Your spy retrieves a person (Deception or Sleight of Hand) by lying to them or drugging and kidnapping them, or object (Sleight of Hand) and attempts to return to you. On a failure, your spy blows their cover and must flee.
• Recall: 1 day. Your spy leaves in the dead of night (Stealth) and returns to you. 

Difficulty Class and Repercussions

When you issue an order, first determine if stealth is needed for the order. If stealth is needed, roll a Stealth Check. If the result is 10 or lower, they have a -2 penalty to the check for the order. If the result is 20 or higher, they have a +2 bonus to the check for the order. Next, roll a d100 and consult the table below to determine the DC for any checks related to completing their order and possible repercussions. Then roll any ability checks for the order, applying their Standing modifier to the roll. A failure typically just means a wasted attempt and you will need to issue another order.

If you roll a 1 on the dice, or if the check fails by 5 or more, then someone suspects your spy. Make a DC 15 Deception Check and apply your Standing modifier. A failure on this check means your spy has blown their cover and must flee.