THE PENTESTER
story blurb
False Friends
introduction
CLASS FEATURES
As a Pentester, you gain the following class
features.
HIT POINTS
Hit Dice: 1d8 per Pentester level
Hit Points at 1st Level: 8 + your Constitution
modifier
Hit Points at Higher Levels: 1d8 (or 5) + your
Constitution modifier per Pentester level
after 1st
PROFICIENCIES
Armor: Light and medium armor
Ranged: Simple and military ranged weapons,
and explosives
Melee: Simple melee weapons
Tools: Hacking tools, electrician’s tools, and
thieves’ tools
Vehicles: Choose any two from: motorcycles,
cars or heavy goods vehicles
Saving Throws: Intelligence, Charisma
Skills: Choose four skills from: Deception,
Espionage, Infiltration,
Infotech, Mechanics, Persuasion, Sleight of
Hand, or Stealth
EQUIPMENT
You start with the following equipment in
addition to any equipment granted to you by
HACKING
your background. While not a Hacker per se, as Pentester you
Choose (a), (b), or (c) from each bullet point: reliy on manipulating computers for most of
(a) a heavy pistol, (b) a taser, or (c) a your work.
submachine gun
(a) A tablet and smartwatch HACKING ACTIONS
(a) Electrician’s tools or (b) thieves’ At 1st level, as an action you can perform one
tools of the following hacking actions:
(a) an undercover vest and
undercover pack Attack. You can make an attack targeting
operating systems or firewalls manually,
against their AC and hit points. Attacking
software follows the rules outlined in Using
Hacking Tools (p163). All hacking attacks deal can make a Wisdom(Infiltration) check, and
coding damage. Making an attack using this add your Charisma modifier as a bonus to
hacking action deals 1d4 coding damage. blend into the scene, as well as observe the
target location.
Bypass. When faced with a protected
Your ability check result becomes the DC for
operating system or password protected
enemy agents to discover your presence.
software you can use the Bypass action in an
attempt to circumvent that security and gain
access to the targeted device. The DC is JACK OF ALL TRADES
based on the complexity of the software or Starting at 2nd level, you can add half your
firewalls installed. proficiency bonus, rounded down, to any
Modify. You can rewrite software in order to ability check you make that doesn’t already
change its function within an operating include your proficiency bonus.
system. Doing so may also alter the function,
or disable other pieces of software. The base PENTESTER ARCHETYPE
DC is 10, modified depending on the At 3rd level, you choose the Pentester
complexity of the software and how many Archetype that
other pieces of software use it within the best suits you. Your choice grants you
operating system, as well as any firewalls features at
present. 3rd level, and again at 9th, 14th, and 17th level.
Patch. You can remove bugs and heal
corruption from ABILITY SCORE IMPROVEMENT
operating systems to bring them back online. When you reach 4th level, and again at 8th,
You must make a DC 15 hacking ability check, 12th, 16th, and 19th level, you can increase one
healing 1d4 coding damage on a success. ability score of your choice by 2, or you can
increase two ability scores of your choice by
HACKING ABILITY 1. As normal, you can’t increase an ability
Intelligence is the skill you use for your score above 20 using this feature.
hacking tools, since you code your tools
through dedicated study and skill. You always EXPERTISE
add your proficiency bonus to hacking At 2nd level, choose two of your skill
actions. proficiencies, or one of your skill
You use your Intelligence whenever a hacking proficiencies and one of your tool
tool refers to your hacking ability. In addition, proficiencies. Your proficiency bonus is
you use your Intelligence modifier when doubled for any ability check you make that
setting the saving throw DC for a hacking tool uses either of the chosen proficiencies. At 6th
you install and when making an attack roll level, you can choose two more of your
with one. proficiencies (in skills or with tools) to gain
this benefit.
Hacking save DC = 8 + your proficiency bonus
+ your Intelligence modifier Cover Identities
Hacking attack modifier = your proficiency
By 5th level you have a multitude of cover
bonus + your Intelligence modifier
identities (including your own true identity).
When you make a hacking attack, you do not They function exactly like real identities, with
add your Intelligence modifier to the damage. practical living conditions and official
documentation. You begin with one cover
THEME identity. Decide the background for this
persona, from the Backgrounds section (p53).
You may establish a pattern of behavior in a
This identity functions as if it were real in
public space, known as a “theme,” in order to
every way, so much so that it is almost
safely gather intelligence about a location, for
infallible as a disguise. You also gain
example a tourist visiting a famous spot, or a
proficiency with disguise kits.
businessperson waiting for a meeting. You
While you have this cover identity, you also
gain access to the equipment granted by its adverse effects. If you use this feature again
background. At 10th level you gain a before you finish a long rest, your personal
second cover identity and at 17th level you OS takes 2d6 coding damage for each caliber
gain a third. of the tool, immediately after you use it. Each
time you use this feature again before
Data Corruption finishing a long rest, the coding damage to
your OS per caliber increases by 1d6. This
Starting at 6th level, your hacking damage
damage ignores any resistance or immunity.
becomes even more potent. The damage from
your hacking Attack action becomes 1d6, and
you add 1d6 bonus damage to any damaging
Hands on Experience
effect from a hacking tool. From 11th level At 18th level, you may use one hacking action
your bonus damage increases to 2d6, and per turn as a bonus action.
from 16th level you bonus damage increases
You may not use the same hacking action
to 3d6.
twice in the same turn.
Rapid Response Diamond Penetrator
Beginning at 7th level, may take a hacking
At 20th level, you are the premier expert in
action against a firewall you triggered this
both technical and social penetration
turn as a reaction.
techniques , applying your knowledge of
computer systems and sociology to gain
Software Update access to places.
Beginning at 10th level, your operating When you are presented with a physical place
system, as well as any firewalls you install, or computer system you wish to access, you
gain a damage threshold equal to your are immediately aware of obvious traps and
proficiency bonus + Intelligence modifier. security meassures.
Your proficiency is doubled for any Charisma
RELIABLE TALENT (Deception) or Intelligence (Infotech) check
By 11th level, you have refined your chosen you make trying to gain access, and you may
skills until they approach perfection. decide to re-roll one of these checks, once,
Whenever you make an ability check that lets while you are on the scene. You may not re-
you add your proficiency bonus, you can treat roll such checks again until you have
a d20 roll of 9 or lower as a 10. completed a short or long rest.
System Forensics
Starting at 13th level, you can automatically
discern the nature and history of an intrusion
into a system you have access to, the result
of the hack, and if any data or software
installed on the system was modified, copied,
or deleted. You also have advantage on
Intelligence (Infotech) checks in order to
deduce the hacking tools used, or the
perpetrator of the attack.
Maximum Payload
Starting at 15th level, you can increase the
power of your simpler software. When you
use a hacking tool that deals damage, you can
deal maximum damage with that attack
rather than rolling for the damage dealt.
The first time you do so, you suffer no
The Pentester Pentester
Level Proficiency Class Features
1st
Bonus
+2 Hacking, Theme
Archetypes
There are distinctive styles of pentesters, the
2nd +2 Jack of all Trades, suave Social Engineer, the technical
Expertise Programming Expert and the agressive Red
3rd +2 Pentester Archetype Team Operator.
feature
4th +2 Ability Score
Social Engineer
Improvement The Social Engineer is a master of
manipulating people and being as
5th +3 Cover Identities
inconspicous as possible at the same time.
6th +3 Data Corruption
7th +3 Rapid Response Corporate Identity
8th +3 Ability Score When you choose this archetype at 3rd level,
Improvement you gain proficiency with forgery kits, you
also gain a free official identity at the
9th +4 Pentester Archetype beginning of each mission. This identity marks
feature you as an employee of a public company, a
10th +4 Software Update member of an military organization, or a
government official in a recognized
11th +4 Reliable Talent
department. You gain the accompanying
12th +4 Ability Score clothing or uniform, and identification for that
Improvement organization for the duration of your mission.
13th +5 System Forensics At the beginning of each mission,
you can maintain this official identity, or
14th +5 Pentester Archetype change it for
feature another.
15th +5 Maximum Payload
16th +5 Ability Score
Cold Reading
Improvement From 9th level, whenever you make a
Charisma (Deception) check against a target,
17th +6 Pentester Archetype
they must make a Charisma saving throw
feature
with a DC equal to 8 + your proficiency
18th +6 Hands on Experience modifier + your Wisdom modifier. If they fail,
19th +6 Ability Score you may learn some basic information about
Improvement that character that they give away from
subtle facial expressions and body language.
20th +6 Diamond Penetrator At the GM’s
discretion, you may instead get information
about the location or situation from their
responses to your leading statements.
Forgetable
By 14th level, you have become so adept at
blending in that anyone trying to remember
you must suceed at a Wisdom saving throw
DC equal to 8 + your proficiency modifier +
your Charisma modifier.
Even if they succeed they can only give a
superficial description of your person and
what you were doing. Red Team Operator
Red Team Operators are the more combat
Teamplayer oriented part of Pentesters.
From 17th level, your leadership and
awareness allows Fighting Style
you to apply tactical thinking in combat
situations. As At 3rd level, when you choose this
an action, you can grant one ally you can specialization, you adopt a particular style of
communicate fighting as your specialty. Choose one of the
with one of the following actions that they following options. You may not choose a
may take Fighting Style option more than once, even if
immediately: Attack, Dodge, or Disengage. you get to choose again later. In addition, you
gain a proficiency with heavy armor, and
Programming Expert heavy ranged weapons.
CQC. You gain a +2 bonus to attack
Programming Experts use their technical
rolls you make
expertise to break into any electrical system
with unarmed or melee weapons. In
and make them do their bidding.
addition, you
can attempt to disarm an opponent
Custom Machine while you are
From 3rd level you customise your pc to your restraining them as a bonus action.
preferences so it fits your demands perfectly. Defense. While you are wearing
Add +2 to all aplicable attributes of your armor, you gain a +1
hacking pc. bonus to AC.
Scrounger Marksmanship. You do not suffer
disadvantage from
From 9th level, you have multiple contacts to attacking at long range with a ranged
gain electrical equipment and can build most weapon.
of the more esoteric stuff yourself from
simple components. Explosives. You can no longer
Half the cost of all hacking and electronics accidentally set off an explosive
equipment. device from a failed ability check, if
you are setting it yourself or
Design Principles attempting to disarm it, unless your
actions would trigger the trap.
From 14th level, when you choose this style, You add your proficiency bonus to
you gain a bonus to any hacking actions equal damage with explosives.
to your Wisdom modifier (minimum 1).
Two-Weapon Fighting. When you
Custom Debug engage in twoweapon fighting, you can
add your ability modifier to the
From 17th level, as an action, you can damage of the second attack.
automatically end one effect of a hacking tool
or action that is affecting your device. In Structural Weaknesses
addition, the DC or Armor Class for the same
tool or action to have the same affect on your From 9th level, you can ignore the damage
device is increased by 5. threshold of objects and vehicles that have
one, and you can ignore any target’s
resistance to explosive damage.
Extra Attack
Beginning at 14th level, you can attack twice,
instead of once, whenever you take the Attack
action on your turn. The number of attacks
increases to three when you reach 18th level
in this class.
Expert Strategist
From 18th level, instead of rolling for
initiative, you can treat your initiative roll
result as a 1, and then add your Intelligence
modifier to all your allies’ initiative rolls
within 60 feet.
