diff --git a/python/cohort/add_github_team_members.py b/python/cohort/add_github_team_members.py
index dafda8a..175385f 100755
--- a/python/cohort/add_github_team_members.py
+++ b/python/cohort/add_github_team_members.py
@@ -1,15 +1,29 @@
 #!/usr/bin/env python3
-"""Add GitHub users to their appropriate teams in nhcarrigan-spring-2026-cohort org"""
+"""Add GitHub users to their appropriate teams in the cohort GitHub organisation.
+
+Uses the GitHub CLI to add each member to their corresponding team and, for
+leaders, to the team's leaders sub-team.
+
+Data files (place in data/):
+  - team_assignments.json   Team rosters with leaders and participants per team
+  - discord_to_github.json  Mapping of Discord IDs to GitHub usernames
+
+Env vars:
+  - None (uses `gh` CLI for authentication)
+"""
 
 import json
 import subprocess
 import time
+from pathlib import Path
+
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
 
 # Load team assignments and Discord to GitHub mappings
-with open("team_assignments.json") as f:
+with open(DATA_DIR / "team_assignments.json") as f:
     teams = json.load(f)
 
-with open("discord_to_github.json") as f:
+with open(DATA_DIR / "discord_to_github.json") as f:
     discord_to_github = json.load(f)
 
 # Map team names to GitHub team slugs
diff --git a/python/cohort/analyse_availability.py b/python/cohort/analyse_availability.py
index 438ee78..723aa98 100644
--- a/python/cohort/analyse_availability.py
+++ b/python/cohort/analyse_availability.py
@@ -1,6 +1,26 @@
+"""Analyse applicant availability from a markdown table and produce UTC block stats.
+
+Reads a markdown table of availability responses and a Discord verification file,
+then produces a JSON summary of coverage across morning/afternoon/evening UTC blocks
+for each day of the week.
+
+Data files (place in data/):
+  - table.md                   Markdown table of applicant availability responses
+  - discord_verification.json  Discord ID verification results (from verify_discord.py)
+
+Outputs (written to data/):
+  - availability_analysis.json  UTC block distribution per applicant
+
+Env vars:
+  - None
+"""
+
 import json
 import re
 from collections import defaultdict
+from pathlib import Path
+
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
 
 DAYS = ["Monday", "Tuesday", "Wednesday", "Thursday", "Friday", "Saturday", "Sunday"]
 
@@ -99,7 +119,7 @@ def analyze_applicant_availability(timezone_str: str, day_slots: dict) -> dict:
 
 def parse_table_md() -> list[dict]:
     """Parse table.md and extract availability data"""
-    with open("table.md") as f:
+    with open(DATA_DIR / "table.md") as f:
         content = f.read()
 
     lines = content.strip().split("\n")
@@ -131,7 +151,7 @@ def parse_table_md() -> list[dict]:
 
 
 def main():
-    with open("discord_verification.json") as f:
+    with open(DATA_DIR / "discord_verification.json") as f:
         verification = json.load(f)
 
     verified_ids = {v[0] for v in verification["verified"]}
@@ -167,7 +187,7 @@ def main():
             }
         )
 
-    with open("availability_analysis.json", "w") as f:
+    with open(DATA_DIR / "availability_analysis.json", "w") as f:
         json.dump(availability_results, f, indent=2)
 
     block_distribution = defaultdict(int)
diff --git a/python/cohort/assign_cohort_role.py b/python/cohort/assign_cohort_role.py
index 97e0ba7..0a9e26f 100644
--- a/python/cohort/assign_cohort_role.py
+++ b/python/cohort/assign_cohort_role.py
@@ -6,9 +6,12 @@ Respects Discord rate limits with proper backoff and retry logic.
 import json
 import os
 import time
+from pathlib import Path
 
 import requests
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 GUILD_ID = "692816967895220344"
 COHORT_ROLE_ID = "1464314780935258112"
@@ -48,7 +51,7 @@ def assign_role_with_retry(user_id: str, role_id: str, max_retries: int = 5) ->
 
 
 def main():
-    with open("team_assignments.json") as f:
+    with open(DATA_DIR / "team_assignments.json") as f:
         teams = json.load(f)
 
     all_users = []
diff --git a/python/cohort/assign_team_roles.py b/python/cohort/assign_team_roles.py
index 91bf134..de162d2 100644
--- a/python/cohort/assign_team_roles.py
+++ b/python/cohort/assign_team_roles.py
@@ -6,9 +6,12 @@ Respects Discord rate limits with proper backoff and retry logic.
 import json
 import os
 import time
+from pathlib import Path
 
 import requests
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 GUILD_ID = "692816967895220344"
 
@@ -64,7 +67,7 @@ def assign_role_with_retry(user_id: str, role_id: str, max_retries: int = 5) ->
 
 
 def main():
-    with open("team_assignments.json") as f:
+    with open(DATA_DIR / "team_assignments.json") as f:
         teams = json.load(f)
 
     print(f"Assigning team roles to {len(teams)} teams...")
diff --git a/python/cohort/catch_up_report.py b/python/cohort/catch_up_report.py
index 2eb948a..41a0d98 100644
--- a/python/cohort/catch_up_report.py
+++ b/python/cohort/catch_up_report.py
@@ -11,9 +11,12 @@ import json
 import os
 import subprocess
 from datetime import datetime, timezone
+from pathlib import Path
 
 import aiohttp
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 DISCORD_BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 DISCORD_API_BASE = "https://discord.com/api/v10"
 GITHUB_API_BASE = "https://api.github.com"
@@ -440,10 +443,10 @@ def build_report(
 async def main() -> None:
     """Run the catch-up activity report."""
     print("Loading data files...")
-    with open("team_assignments.json") as f:
+    with open(DATA_DIR / "team_assignments.json") as f:
         team_data: list[dict] = json.load(f)
 
-    with open("discord_to_github.json") as f:
+    with open(DATA_DIR / "discord_to_github.json") as f:
         discord_to_github: dict[str, str] = json.load(f)
 
     print("Getting GitHub token via gh CLI...")
diff --git a/python/cohort/check_lengths.py b/python/cohort/check_lengths.py
index a4a39f6..9ef5343 100644
--- a/python/cohort/check_lengths.py
+++ b/python/cohort/check_lengths.py
@@ -1,4 +1,15 @@
-"""Quick dry-run to check Discord message lengths before sending."""
+"""Dry-run check of Discord message lengths before sending the activity report.
+
+Parses the catch_up_report.md table, formats each team's data into a monospace
+Discord table, and reports whether any message would exceed Discord's 2000-char limit.
+Run this before send_activity_report.py to catch length issues early.
+
+Data files (place in data/):
+  - catch_up_report.md  Activity report generated by catch_up_report.py
+
+Env vars:
+  - None
+"""
 
 FIELDS = [
     ("Discord Username", "Name", 18),
@@ -11,7 +22,7 @@ FIELDS = [
     ("Commits", "Commits", 7),
 ]
 
-REPORT_PATH = "catch_up_report.md"
+REPORT_PATH = "data/catch_up_report.md"
 
 
 def parse_report(path: str) -> dict[str, list[dict]]:
diff --git a/python/cohort/discord_activity_checker.py b/python/cohort/discord_activity_checker.py
index c23184f..e6cda78 100755
--- a/python/cohort/discord_activity_checker.py
+++ b/python/cohort/discord_activity_checker.py
@@ -1,6 +1,17 @@
 #!/usr/bin/env python3
-"""Discord Team Activity Checker
-Checks for team members who haven't sent messages in their channels within 36 hours
+"""Check for team members who have not sent a message in their channel within 36 hours.
+
+Scans each team's Discord channel and flags members with no recent activity.
+Optionally sends a direct mention message to inactive members.
+
+Data files (place in data/):
+  - team_assignments.json  Team rosters with leaders and participants per team
+
+Outputs (written to data/):
+  - discord_activity_report.json  Inactive members per team with last-seen timestamps
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
 """
 
 import asyncio
@@ -8,16 +19,19 @@ import json
 import os
 import sys
 from datetime import datetime, timedelta, timezone
+from pathlib import Path
 
 import aiohttp
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 # Configuration
 DISCORD_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 DISCORD_API_BASE = "https://discord.com/api/v10"
 INACTIVE_THRESHOLD_HOURS = 36
 
 # Load team assignments from file
-with open("team_assignments.json") as f:
+with open(DATA_DIR / "team_assignments.json") as f:
     team_data = json.load(f)
 
 # Build TEAMS dictionary with channel IDs and member lists
@@ -233,7 +247,7 @@ async def main():
         print("\n" + "=" * 80)
 
         # Save results to JSON
-        with open("discord_activity_report.json", "w") as f:
+        with open(DATA_DIR / "discord_activity_report.json", "w") as f:
             json.dump(
                 {
                     "generated_at": datetime.now(timezone.utc).isoformat(),
diff --git a/python/cohort/evaluate_technical_proficiency.py b/python/cohort/evaluate_technical_proficiency.py
index b31d50b..86393ae 100644
--- a/python/cohort/evaluate_technical_proficiency.py
+++ b/python/cohort/evaluate_technical_proficiency.py
@@ -1,8 +1,27 @@
+"""Evaluate the technical proficiency of cohort applicants using their GitHub profiles.
+
+Fetches each applicant's public GitHub repositories and scores their proficiency as
+Beginner, Intermediate, or Advanced based on language variety, repo count, commit
+activity, and presence of certain technologies.
+
+Data files (place in data/):
+  - applicants_to_evaluate.json  List of applicants with GitHub usernames
+
+Outputs (written to data/):
+  - proficiency_evaluations.json  Proficiency scores and tech stacks per applicant
+
+Env vars:
+  - None (uses public GitHub API; may be rate-limited without authentication)
+"""
+
 import json
 import re
 import time
 import urllib.error
 import urllib.request
+from pathlib import Path
+
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
 
 # GitHub API (no auth needed for public repos, but rate limited)
 GITHUB_API = "https://api.github.com"
@@ -234,7 +253,7 @@ def evaluate_applicant(applicant: dict, index: int, total: int) -> dict:
 
 def main():
     # Load applicants
-    with open("applicants_to_evaluate.json") as f:
+    with open(DATA_DIR / "applicants_to_evaluate.json") as f:
         applicants = json.load(f)
 
     print(f"Evaluating {len(applicants)} applicants...\n")
@@ -249,7 +268,7 @@ def main():
             print(f"  Progress: {i + 1}/{len(applicants)} complete")
 
     # Save results
-    with open("proficiency_evaluations.json", "w") as f:
+    with open(DATA_DIR / "proficiency_evaluations.json", "w") as f:
         json.dump(evaluations, f, indent=2)
 
     # Summary
diff --git a/python/cohort/fix_channel_permissions.py b/python/cohort/fix_channel_permissions.py
index f159d7b..c257609 100644
--- a/python/cohort/fix_channel_permissions.py
+++ b/python/cohort/fix_channel_permissions.py
@@ -1,7 +1,15 @@
 #!/usr/bin/env python3
-"""Fix permissions for cohort-team-michael-and-yoon channel.
+"""Fix Send Messages / Send Messages in Threads permissions for a Discord channel.
 
-Deny Send Messages in Threads for @everyone and @cohort.
+Denies Send Messages and Send Messages in Threads for both @everyone and the
+@cohort role on the target channel. Update CHANNEL_ID and COHORT_ROLE_ID before
+running.
+
+Data files (place in data/):
+  - None
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
 """
 
 import asyncio
diff --git a/python/cohort/generate_member_files.py b/python/cohort/generate_member_files.py
index 8ce6749..663eccb 100644
--- a/python/cohort/generate_member_files.py
+++ b/python/cohort/generate_member_files.py
@@ -1,23 +1,46 @@
+"""Generate markdown participant and leader profile files for the cohort.
+
+Reads all evaluation data files and produces two markdown files summarising
+each member's tech stack, availability, proficiency, and leadership assessment.
+
+Data files (place in data/):
+  - discord_verification.json   Discord ID verification results (from verify_discord.py)
+  - proficiency_evaluations.json  Proficiency scores (from evaluate_technical_proficiency.py)
+  - availability_analysis.json  Availability UTC blocks (from analyse_availability.py)
+  - leadership_candidates.json  List of applicants who expressed interest in leading
+  - leadership_evaluations.json  Leadership assessment scores
+
+Outputs (written to data/):
+  - participants.md  Markdown profile for each participant
+  - leaders.md       Markdown profile for each leader candidate
+
+Env vars:
+  - None
+"""
+
 import json
+from pathlib import Path
+
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
 
 BLOCK_EMOJIS = {"mornings": "🌅", "afternoons": "☀️", "evenings": "🌆", "nights": "🌙"}
 
 
 def load_all_data():
     """Load all evaluation data files"""
-    with open("discord_verification.json") as f:
+    with open(DATA_DIR / "discord_verification.json") as f:
         verification = json.load(f)
 
-    with open("proficiency_evaluations.json") as f:
+    with open(DATA_DIR / "proficiency_evaluations.json") as f:
         proficiency = json.load(f)
 
-    with open("availability_analysis.json") as f:
+    with open(DATA_DIR / "availability_analysis.json") as f:
         availability = json.load(f)
 
-    with open("leadership_candidates.json") as f:
+    with open(DATA_DIR / "leadership_candidates.json") as f:
         candidates = json.load(f)
 
-    with open("leadership_evaluations.json") as f:
+    with open(DATA_DIR / "leadership_evaluations.json") as f:
         leadership = json.load(f)
 
     return verification, proficiency, availability, candidates, leadership
@@ -230,14 +253,14 @@ def main():
     participants_md = generate_participants_md(
         non_leader_ids, verified_usernames, prof_by_id, avail_by_id
     )
-    with open("participants.md", "w") as f:
+    with open(DATA_DIR / "participants.md", "w") as f:
         f.write(participants_md)
     print(f"Generated participants.md with {len(non_leader_ids)} participants")
 
     leaders_md = generate_leaders_md(
         leader_ids, verified_usernames, prof_by_id, avail_by_id, lead_by_id
     )
-    with open("leaders.md", "w") as f:
+    with open(DATA_DIR / "leaders.md", "w") as f:
         f.write(leaders_md)
     print(f"Generated leaders.md with {len(leader_ids)} leaders")
 
diff --git a/python/cohort/generate_timeslots.py b/python/cohort/generate_timeslots.py
index 9492877..2b44116 100644
--- a/python/cohort/generate_timeslots.py
+++ b/python/cohort/generate_timeslots.py
@@ -1,5 +1,20 @@
+"""Generate hourly timeslot JSON for use with Crabfit scheduling tool.
+
+Produces a list of ISO-format datetime strings covering every hour across the
+scheduling window. Update the start_date and end_date constants before running.
+
+Outputs (written to data/):
+  - crabfit_timeslots.json  List of hourly timeslot strings
+
+Env vars:
+  - None
+"""
+
 import json
 from datetime import datetime, timedelta
+from pathlib import Path
+
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
 
 # Generate hourly time slots from Feb 1 to March 3, 2026
 # 24 hours a day, America/Los_Angeles timezone
@@ -18,7 +33,7 @@ print(f"First: {times[0]}")
 print(f"Last: {times[-1]}")
 
 # Save to file for use
-with open("/home/naomi/docs/cohort/crabfit_timeslots.json", "w") as f:
+with open(DATA_DIR / "crabfit_timeslots.json", "w") as f:
     json.dump(times, f)
 
 print("Saved to crabfit_timeslots.json")
diff --git a/python/cohort/get_cohort_members.py b/python/cohort/get_cohort_members.py
index 4ad2940..0b588c8 100644
--- a/python/cohort/get_cohort_members.py
+++ b/python/cohort/get_cohort_members.py
@@ -4,9 +4,12 @@
 import asyncio
 import json
 import os
+from pathlib import Path
 
 import aiohttp
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 DISCORD_BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 GUILD_ID = "692816967895220344"
 COHORT_ROLE_ID = "1464314780935258112"
@@ -72,7 +75,7 @@ async def main() -> None:
                 f"{i}. {member['display_name']} (@{member['username']}) - ID: {member['id']}"  # noqa: E501
             )
 
-        with open("active_cohort_members.json", "w") as f:
+        with open(DATA_DIR / "active_cohort_members.json", "w") as f:
             json.dump(cohort_members, f, indent=2)
 
         print("\nSaved to active_cohort_members.json")
diff --git a/python/cohort/remove_discord_roles.py b/python/cohort/remove_discord_roles.py
index b0149a6..6d2b15b 100644
--- a/python/cohort/remove_discord_roles.py
+++ b/python/cohort/remove_discord_roles.py
@@ -1,5 +1,15 @@
 #!/usr/bin/env python3
-"""Remove cohort and team roles from inactive Discord members."""
+"""Remove the Cohort and team-specific Discord roles from a list of members.
+
+Update INACTIVE_MEMBERS and MEMBER_TO_TEAM before running to target the correct
+members. Removes both the cohort-wide role and the member's team role.
+
+Data files (place in data/):
+  - None (member IDs and team mappings are defined as constants in the script)
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
+"""
 
 import asyncio
 import os
diff --git a/python/cohort/remove_member.py b/python/cohort/remove_member.py
index acccb45..3eb27e0 100644
--- a/python/cohort/remove_member.py
+++ b/python/cohort/remove_member.py
@@ -18,9 +18,12 @@ import json
 import os
 import sys
 from datetime import datetime, timezone
+from pathlib import Path
 
 import aiohttp
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 DISCORD_BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 DISCORD_API_BASE = "https://discord.com/api/v10"
 DISCORD_GUILD_ID = "692816967895220344"
@@ -71,7 +74,7 @@ class MemberRemover:
 
     def find_member_info(self) -> bool:
         """Find which team the member is on and their role."""
-        with open("team_assignments.json") as f:
+        with open(DATA_DIR / "team_assignments.json") as f:
             teams = json.load(f)
 
         for team in teams:
@@ -88,7 +91,7 @@ class MemberRemover:
 
     def remove_from_team_assignments(self) -> None:
         """Remove member from team_assignments.json."""
-        with open("team_assignments.json") as f:
+        with open(DATA_DIR / "team_assignments.json") as f:
             teams = json.load(f)
 
         for team in teams:
@@ -103,19 +106,19 @@ class MemberRemover:
                     f"✅ Removed from {team['name']} participants in team_assignments.json"
                 )
 
-        with open("team_assignments.json", "w") as f:
+        with open(DATA_DIR / "team_assignments.json", "w") as f:
             json.dump(teams, f, indent=2)
 
     def remove_from_discord_to_github(self) -> None:
         """Remove member from discord_to_github.json."""
-        with open("discord_to_github.json") as f:
+        with open(DATA_DIR / "discord_to_github.json") as f:
             mappings = json.load(f)
 
         if self.discord_id in mappings:
             self.github_username = mappings[self.discord_id]
             del mappings[self.discord_id]
 
-            with open("discord_to_github.json", "w") as f:
+            with open(DATA_DIR / "discord_to_github.json", "w") as f:
                 json.dump(mappings, f, indent=2)
 
             print(f"✅ Removed {self.github_username} from discord_to_github.json")
@@ -135,7 +138,7 @@ class MemberRemover:
 
     async def remove_discord_roles(self) -> None:
         """Remove Discord roles from the member."""
-        with open("team_message_ids.json") as f:
+        with open(DATA_DIR / "team_message_ids.json") as f:
             team_message_data = json.load(f)
 
         if self.team_name not in team_message_data:
diff --git a/python/cohort/remove_resigned_members.py b/python/cohort/remove_resigned_members.py
index 8c7a029..5f79cf1 100644
--- a/python/cohort/remove_resigned_members.py
+++ b/python/cohort/remove_resigned_members.py
@@ -6,6 +6,9 @@ before running this script.
 """
 
 import json
+from pathlib import Path
+
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
 
 # Discord IDs of members who have resigned - update before running
 RESIGNED_IDS: list[str] = []
@@ -13,7 +16,7 @@ RESIGNED_IDS: list[str] = []
 
 def main() -> None:
     """Remove resigned members from team assignments."""
-    with open("team_assignments.json") as f:
+    with open(DATA_DIR / "team_assignments.json") as f:
         teams = json.load(f)
 
     changes_made = []
@@ -36,7 +39,7 @@ def main() -> None:
             changes_made.append(f"Removed {removed} participant(s) from {team_name}")
             print(f"⚠️  {team_name}: Proficiency distribution may need updating")
 
-    with open("team_assignments.json", "w") as f:
+    with open(DATA_DIR / "team_assignments.json", "w") as f:
         json.dump(teams, f, indent=2)
 
     if changes_made:
diff --git a/python/cohort/send_activity_report.py b/python/cohort/send_activity_report.py
index 01b2914..4832e19 100644
--- a/python/cohort/send_activity_report.py
+++ b/python/cohort/send_activity_report.py
@@ -1,4 +1,14 @@
-"""Send formatted activity report tables to each team channel via Amari bot."""
+"""Send formatted activity report tables to each team's Discord channel.
+
+Parses catch_up_report.md and posts a monospace table of each member's Discord
+and GitHub activity stats to their respective team channel.
+
+Data files (place in data/):
+  - catch_up_report.md  Activity report generated by catch_up_report.py
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
+"""
 
 import asyncio
 import os
@@ -25,7 +35,9 @@ CHANNEL_IDS = {
     "Sage Marigold": "1464316850669093040",
 }
 
-REPORT_PATH = os.path.join(os.path.dirname(__file__), "catch_up_report.md")
+REPORT_PATH = os.path.join(
+    os.path.dirname(__file__), "..", "..", "data", "catch_up_report.md"
+)
 
 FIELDS = [
     ("Discord Username", "Name", 18),
diff --git a/python/cohort/send_checkin.py b/python/cohort/send_checkin.py
index 26b142c..9515381 100644
--- a/python/cohort/send_checkin.py
+++ b/python/cohort/send_checkin.py
@@ -1,11 +1,25 @@
-"""Send check-in messages to all team channels."""
+"""Send biweekly check-in messages to all team Discord channels.
+
+Posts a check-in prompt to each team channel and automatically creates a thread
+for responses. Members who do not respond by the deadline may be removed for
+inactivity.
+
+Data files (place in data/):
+  - team_message_ids.json  Channel IDs per team (generated by send_team_messages.py)
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
+"""
 
 import asyncio
 import json
 import os
+from pathlib import Path
 
 import aiohttp
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 DISCORD_BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 DISCORD_API = "https://discord.com/api/v10"
 GUILD_ID = "692816967895220344"
@@ -22,7 +36,7 @@ CHECK_IN_MESSAGE = """@everyone it is time for Naomi to do a check in. I need **
 
 async def send_checkin_to_teams() -> None:
     """Send check-in message to all team channels (except Jade Jasmine)."""
-    with open("team_message_ids.json") as f:
+    with open(DATA_DIR / "team_message_ids.json") as f:
         team_data = json.load(f)
 
     headers = {
diff --git a/python/cohort/send_team_checkin.py b/python/cohort/send_team_checkin.py
index dc66071..0fc6724 100644
--- a/python/cohort/send_team_checkin.py
+++ b/python/cohort/send_team_checkin.py
@@ -1,12 +1,26 @@
 #!/usr/bin/env python3
-"""Send team check-in messages to all 14 teams."""
+"""Send a capacity check-in message to each team channel.
+
+Posts a message asking whether the team feels able to complete their project
+given their current member count, and invites them to request support if needed.
+
+Data files (place in data/):
+  - team_message_ids.json   Channel and role IDs per team (from send_team_messages.py)
+  - team_assignments.json   Team rosters used to report current member counts
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
+"""
 
 import asyncio
 import json
 import os
+from pathlib import Path
 
 import aiohttp
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 DISCORD_BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 NAOMI_ID = "465650873650118659"
 
@@ -58,10 +72,10 @@ async def send_message(
 
 async def main() -> None:
     """Send check-in messages to all teams."""
-    with open("team_message_ids.json") as f:
+    with open(DATA_DIR / "team_message_ids.json") as f:
         team_data = json.load(f)
 
-    with open("team_assignments.json") as f:
+    with open(DATA_DIR / "team_assignments.json") as f:
         teams = json.load(f)
 
     async with aiohttp.ClientSession() as session:
diff --git a/python/cohort/send_team_messages.py b/python/cohort/send_team_messages.py
index 0ee6bb0..c9b69bb 100644
--- a/python/cohort/send_team_messages.py
+++ b/python/cohort/send_team_messages.py
@@ -1,10 +1,29 @@
+"""Send initial welcome and roster messages to all team Discord channels.
+
+Creates a pinned roster message in each team channel and stores the resulting
+message ID, channel ID, and role ID in team_message_ids.json for use by
+other scripts (send_checkin.py, update_roster_messages.py, etc.).
+
+Data files (place in data/):
+  - team_assignments.json       Team rosters with leaders and participants per team
+  - applicants_to_evaluate.json  Applicant data including Discord channel/role IDs
+
+Outputs (written to data/):
+  - team_message_ids.json  Channel ID, message ID, and role ID per team
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
+"""
+
 import json
 import os
 import time
+from pathlib import Path
 
 import requests
 
-# Amari's bot token
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 GUILD_ID = "692816967895220344"
 
@@ -72,12 +91,12 @@ TEAMS = {
 }
 
 # Load team assignments and convert to dict by team name
-with open("team_assignments.json") as f:
+with open(DATA_DIR / "team_assignments.json") as f:
     team_list = json.load(f)
     team_data = {team["name"]: team for team in team_list}
 
 # Load applicants to get project_url by discord_id
-with open("applicants_to_evaluate.json") as f:
+with open(DATA_DIR / "applicants_to_evaluate.json") as f:
     applicants = json.load(f)
     applicant_lookup = {str(a["discord_id"]): a for a in applicants}
 
diff --git a/python/cohort/update_roster_messages.py b/python/cohort/update_roster_messages.py
index d181ba9..378ee41 100644
--- a/python/cohort/update_roster_messages.py
+++ b/python/cohort/update_roster_messages.py
@@ -3,9 +3,12 @@
 import asyncio
 import json
 import os
+from pathlib import Path
 
 import aiohttp
 
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
+
 DISCORD_BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
 GUILD_ID = "692816967895220344"
 
@@ -62,13 +65,13 @@ def generate_roster(team: dict, discord_to_github: dict) -> str:
 
 async def main() -> None:
     """Update roster messages for all teams."""
-    with open("team_message_ids.json") as f:
+    with open(DATA_DIR / "team_message_ids.json") as f:
         team_data = json.load(f)
 
-    with open("team_assignments.json") as f:
+    with open(DATA_DIR / "team_assignments.json") as f:
         teams = json.load(f)
 
-    with open("discord_to_github.json") as f:
+    with open(DATA_DIR / "discord_to_github.json") as f:
         discord_to_github = json.load(f)
 
     async with aiohttp.ClientSession() as session:
diff --git a/python/cohort/verify_discord.py b/python/cohort/verify_discord.py
index e9894c8..d4bd09a 100644
--- a/python/cohort/verify_discord.py
+++ b/python/cohort/verify_discord.py
@@ -1,8 +1,26 @@
+"""Verify Discord user IDs from a markdown table of applicant data.
+
+Reads a markdown table containing Discord IDs and checks each one against the
+Discord API to confirm the user exists. Handles rate limits automatically.
+
+Data files (place in data/):
+  - table.md  Markdown table of applicants including a Discord ID column
+
+Outputs (written to data/):
+  - discord_verification.json  Verification result (valid/invalid) per Discord ID
+
+Env vars:
+  - DISCORD_BOT_TOKEN  Bot token for the Discord API
+"""
+
 import json
 import os
 import time
 import urllib.error
 import urllib.request
+from pathlib import Path
+
+DATA_DIR = Path(__file__).parent.parent.parent / "data"
 
 # Configuration
 BOT_TOKEN = os.environ["DISCORD_BOT_TOKEN"]
@@ -10,7 +28,7 @@ GUILD_ID = "692816967895220344"
 BASE_URL = "https://discord.com/api/v10"
 
 # Read Discord IDs from table.md
-with open("table.md") as f:
+with open(DATA_DIR / "table.md") as f:
     content = f.read()
 
 lines = content.strip().split("\n")
@@ -104,7 +122,7 @@ print(f"Missing: {len(missing)}")
 print(f"Errors: {len(errors)}")
 
 # Save results
-with open("discord_verification.json", "w") as f:
+with open(DATA_DIR / "discord_verification.json", "w") as f:
     json.dump({"verified": verified, "missing": missing, "errors": errors}, f, indent=2)
 
 print("\nResults saved to discord_verification.json")
diff --git a/typescript/src/crowdin/clearHiddenTranslations.ts b/typescript/src/crowdin/clearHiddenTranslations.ts
index 325dff4..efb32f7 100644
--- a/typescript/src/crowdin/clearHiddenTranslations.ts
+++ b/typescript/src/crowdin/clearHiddenTranslations.ts
@@ -1,4 +1,15 @@
 /**
+ * @file Delete hidden/outdated translations from a Crowdin project.
+ * Reads a list of string IDs from data/crowdin-strings.json, checks which
+ * have already been processed via the log file, and deletes translations
+ * for unprocessed strings across all active languages in parallel.
+ * Data files (place in data/):
+ * - crowdin-strings.json       String IDs to clear (from crowdin/writeData.ts)
+ * - crowdin-strings-hidden.txt Log of already-processed string IDs
+ * Env vars:
+ * CROWDIN_PROJECT_ID - Crowdin project numeric ID
+ * CROWDIN_API_URL    - Base URL of the Crowdin API
+ * CROWDIN_TOKEN      - Crowdin personal access token.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/crowdin/reapplyTranslations.ts b/typescript/src/crowdin/reapplyTranslations.ts
index 52468a9..581a014 100644
--- a/typescript/src/crowdin/reapplyTranslations.ts
+++ b/typescript/src/crowdin/reapplyTranslations.ts
@@ -1,4 +1,12 @@
 /**
+ * @file Trigger a pre-translation run on a Crowdin project and wait for completion.
+ * Fetches all active languages and files, submits a pre-translation request,
+ * and polls for progress every 5 seconds until it reaches 100%%.
+ * Data files: None
+ * Env vars:
+ * CROWDIN_PROJECT_ID - Crowdin project numeric ID
+ * CROWDIN_API_URL    - Base URL of the Crowdin API
+ * CROWDIN_TOKEN      - Crowdin personal access token.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/discord/cycThreads.ts b/typescript/src/discord/cycThreads.ts
index 6a752b7..8eb08fb 100644
--- a/typescript/src/discord/cycThreads.ts
+++ b/typescript/src/discord/cycThreads.ts
@@ -1,4 +1,10 @@
 /**
+ * @file Create discussion threads for CYC talk submissions in a Discord channel.
+ * Iterates over a hardcoded list of talk titles and speakers and creates a
+ * Discord forum thread for each one. Update the data array and CHANNEL_ID before running.
+ * Data files: None (talk data is hardcoded in the script)
+ * Env vars:
+ * DISCORD_TOKEN - Bot token for the Discord API.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/discord/guildCount.ts b/typescript/src/discord/guildCount.ts
index 668dd6b..36db36b 100644
--- a/typescript/src/discord/guildCount.ts
+++ b/typescript/src/discord/guildCount.ts
@@ -1,4 +1,14 @@
 /**
+ * @file Count and categorise all Discord servers a user belongs to.
+ * Uses the Discord OAuth2 PKCE flow with a local callback server to authenticate,
+ * then fetches and categorises all guilds (owned, admin, moderated, partnered,
+ * verified, community, discoverable) and serves an HTML dashboard on localhost.
+ * Data files: None
+ * Env vars:
+ * DISCORD_CLIENT_ID     - OAuth2 application client ID
+ * DISCORD_CLIENT_SECRET - OAuth2 application client secret (optional)
+ * DISCORD_REDIRECT_URI  - OAuth2 redirect URI (default: http://127.0.0.1:8721/callback)
+ * DISCORD_SCOPES        - OAuth2 scopes (default: identify guilds).
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/discourse/bulkUpdateCategories.ts b/typescript/src/discourse/bulkUpdateCategories.ts
index 0110298..c9d5f05 100644
--- a/typescript/src/discourse/bulkUpdateCategories.ts
+++ b/typescript/src/discourse/bulkUpdateCategories.ts
@@ -1,4 +1,12 @@
 /**
+ * @file Set auto-close settings on all Discourse forum categories.
+ * Fetches all categories and subcategories and enables auto-close based on
+ * last post (672 hours / 28 days) for each one.
+ * Data files: None
+ * Env vars:
+ * DISCOURSE_URL          - Base URL of the Discourse instance
+ * DISCOURSE_API_KEY      - Discourse API key
+ * DISCOURSE_API_USERNAME - Discourse API username.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/discourse/closeOldTopics.ts b/typescript/src/discourse/closeOldTopics.ts
index daea1a1..410b98c 100644
--- a/typescript/src/discourse/closeOldTopics.ts
+++ b/typescript/src/discourse/closeOldTopics.ts
@@ -1,4 +1,11 @@
 /**
+ * @file Close inactive Discourse topics that have had no activity for 28+ days.
+ * Skips topics older than 6 months (already archived) and any that are already closed.
+ * Data files: None
+ * Env vars:
+ * DISCOURSE_URL          - Base URL of the Discourse instance
+ * DISCOURSE_API_KEY      - Discourse API key
+ * DISCOURSE_API_USERNAME - Discourse API username.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/gitea/deleteFromAllRepos.ts b/typescript/src/gitea/deleteFromAllRepos.ts
index 0814539..421e959 100644
--- a/typescript/src/gitea/deleteFromAllRepos.ts
+++ b/typescript/src/gitea/deleteFromAllRepos.ts
@@ -1,4 +1,10 @@
 /**
+ * @file Delete a file from every repository across all nhcarrigan Gitea orgs.
+ * Prompts for the file path to delete, then removes it from every repo
+ * across nhcarrigan, nhcarrigan-private, and nhcarrigan-games.
+ * Data files: None
+ * Env vars:
+ * GITEA_TOKEN - Gitea personal access token with repo write permissions.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/gitea/uploadToAllRepos.ts b/typescript/src/gitea/uploadToAllRepos.ts
index 74a0dc6..8d0f304 100644
--- a/typescript/src/gitea/uploadToAllRepos.ts
+++ b/typescript/src/gitea/uploadToAllRepos.ts
@@ -1,4 +1,11 @@
 /**
+ * @file Upload a file from data/ to every repository across all nhcarrigan Gitea orgs.
+ * Prompts for the local filename and destination path, then creates or updates
+ * the file in every repo across nhcarrigan, nhcarrigan-private, and nhcarrigan-games.
+ * Data files (place in data/):
+ * - Any file to upload (prompted interactively)
+ * Env vars:
+ * GITEA_TOKEN - Gitea personal access token with repo write permissions.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/gitea/uploadToReposConditionally.ts b/typescript/src/gitea/uploadToReposConditionally.ts
index 90f540c..a93d3b8 100644
--- a/typescript/src/gitea/uploadToReposConditionally.ts
+++ b/typescript/src/gitea/uploadToReposConditionally.ts
@@ -1,4 +1,11 @@
 /**
+ * @file Conditionally upload a file to Gitea repos based on whether another file exists.
+ * Prompts for the file to upload, a condition file path, and whether to upload
+ * when the condition file exists or does not exist.
+ * Data files (place in data/):
+ * - Any file to upload (prompted interactively)
+ * Env vars:
+ * GITEA_TOKEN - Gitea personal access token with repo write permissions.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/github/auditNpmPackages.ts b/typescript/src/github/auditNpmPackages.ts
index 5a65d06..dda69f5 100644
--- a/typescript/src/github/auditNpmPackages.ts
+++ b/typescript/src/github/auditNpmPackages.ts
@@ -1,4 +1,12 @@
 /**
+ * @file Audit npm packages across a GitHub organisation for known vulnerabilities.
+ * Lists all repositories in the target org, fetches each package.json, and checks
+ * for usage of packages in the hardcoded vulnerable package list.
+ * Update the vulnerable package list and orgName constant before running.
+ * Outputs (written to data/):
+ * - npm-vulnerabilities.txt  Repos and packages with vulnerability findings
+ * Env vars:
+ * GITHUB_TOKEN - GitHub personal access token with org read permissions.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/github/onboardMentee.ts b/typescript/src/github/onboardMentee.ts
index 0c704ef..5129925 100644
--- a/typescript/src/github/onboardMentee.ts
+++ b/typescript/src/github/onboardMentee.ts
@@ -1,4 +1,12 @@
 /**
+ * @file Onboard a new mentee to the nhcarrigan-mentorship GitHub organisation.
+ * Prompts for the mentee's Discord ID, full name, and GitHub username, creates
+ * a personal repository in the org, adds the mentee as a collaborator with
+ * maintain permissions, and posts a welcome message to the Discord channel.
+ * Data files: None
+ * Env vars:
+ * GITHUB_TOKEN  - GitHub personal access token with org and repo permissions
+ * DISCORD_TOKEN - Bot token for the Discord API.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/github/postUserStories.ts b/typescript/src/github/postUserStories.ts
index c2cc618..4e85f64 100644
--- a/typescript/src/github/postUserStories.ts
+++ b/typescript/src/github/postUserStories.ts
@@ -1,4 +1,11 @@
 /**
+ * @file Post user story markdown files as GitHub issue descriptions.
+ * Reads all markdown files from data/stories/ and updates the corresponding
+ * GitHub issue with that content. Filename format: {repo-name}-{issue-number}.md.
+ * Data files (place in data/stories/):
+ * - {repo-name}-{issue-number}.md  User story content for each issue
+ * Env vars:
+ * GITHUB_TOKEN - GitHub personal access token with repo write permissions.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/music/id3v2.ts b/typescript/src/music/id3v2.ts
index 1055f89..d06392b 100644
--- a/typescript/src/music/id3v2.ts
+++ b/typescript/src/music/id3v2.ts
@@ -1,4 +1,10 @@
 /**
+ * @file Tag MP3 files with ID3v2 metadata and album art for Neuro-sama tracks.
+ * Reads all MP3 files from the download directory, extracts the title from
+ * the filename, sets the artist to "Neuro-sama", and applies the cover image.
+ * Update the directory and cover constants before running.
+ * Data files: None (reads from a local directory path defined in the script)
+ * Env vars: None (uses eyeD3 and id3v2 CLI tools).
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/s3/bulkUpload.ts b/typescript/src/s3/bulkUpload.ts
index c7ef695..d9341fb 100644
--- a/typescript/src/s3/bulkUpload.ts
+++ b/typescript/src/s3/bulkUpload.ts
@@ -1,4 +1,13 @@
 /**
+ * @file Upload all files in the data/ directory to an S3-compatible bucket.
+ * Displays a tree of files to upload, prompts for confirmation, then uploads
+ * with a progress bar showing per-file status.
+ * Data files (place in data/):
+ * - All files to upload are read from the data/ directory recursively
+ * Env vars:
+ * AWS_ACCESS_KEY_ID     - S3 access key
+ * AWS_SECRET_ACCESS_KEY - S3 secret key
+ * S3_ENDPOINT           - S3-compatible endpoint URL.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/s3/correctContentType.ts b/typescript/src/s3/correctContentType.ts
index 29a8824..a97ebfc 100644
--- a/typescript/src/s3/correctContentType.ts
+++ b/typescript/src/s3/correctContentType.ts
@@ -1,4 +1,12 @@
 /**
+ * @file Fix incorrect Content-Type metadata on objects in an S3-compatible bucket.
+ * Lists all objects, detects MIME type from extension, and re-uploads metadata
+ * for any file whose stored Content-Type does not match the expected type.
+ * Data files: None
+ * Env vars:
+ * AWS_ACCESS_KEY_ID     - S3 access key
+ * AWS_SECRET_ACCESS_KEY - S3 secret key
+ * S3_ENDPOINT           - S3-compatible endpoint URL.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/s3/deleteContents.ts b/typescript/src/s3/deleteContents.ts
index a145600..cd30454 100644
--- a/typescript/src/s3/deleteContents.ts
+++ b/typescript/src/s3/deleteContents.ts
@@ -1,4 +1,12 @@
 /**
+ * @file Delete all objects from an S3-compatible bucket.
+ * Prompts for the bucket name, requires double confirmation (type name + yes/no),
+ * then lists and deletes all objects in batches with a progress bar.
+ * Data files: None
+ * Env vars:
+ * AWS_ACCESS_KEY_ID     - S3 access key
+ * AWS_SECRET_ACCESS_KEY - S3 secret key
+ * S3_ENDPOINT           - S3-compatible endpoint URL.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/s3/upload.ts b/typescript/src/s3/upload.ts
index d046285..233c417 100644
--- a/typescript/src/s3/upload.ts
+++ b/typescript/src/s3/upload.ts
@@ -1,4 +1,12 @@
 /**
+ * @file Upload a single file from the data/ directory to an S3-compatible bucket.
+ * Prompts for the local filename and the destination path in the bucket.
+ * Data files (place in data/):
+ * - Any file to upload (prompted interactively)
+ * Env vars:
+ * AWS_ACCESS_KEY_ID     - S3 access key
+ * AWS_SECRET_ACCESS_KEY - S3 secret key
+ * S3_ENDPOINT           - S3-compatible endpoint URL.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan
diff --git a/typescript/src/security/generateReport.ts b/typescript/src/security/generateReport.ts
index f5aa469..8dbac63 100644
--- a/typescript/src/security/generateReport.ts
+++ b/typescript/src/security/generateReport.ts
@@ -1,5 +1,12 @@
 /* eslint-disable max-lines -- Necessary for all of the HTML templating. */
 /**
+ * @file Generate a public HTML security report from DefectDojo findings.
+ * Fetches all active, verified findings from DefectDojo and produces a styled
+ * HTML dashboard grouped by project with severity counts.
+ * Outputs (written to data/):
+ * - public_security_report.html  HTML security report
+ * Env vars:
+ * DOJO_TOKEN - DefectDojo API token.
  * @copyright NHCarrigan
  * @license Naomi's Public License
  * @author Naomi Carrigan