diff --git a/CLAUDE.md b/CLAUDE.md
index a66f2e1..13eeb3c 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -51,10 +51,29 @@ When working with specific technologies, automatically load their dedicated cont
   - Note: Windows desktop monitoring with Discord notifications available
   - Note: Comprehensive Tdarr API monitoring with dataclass-based status tracking
 
+**Productivity Keywords**
+- "task", "todo", "productivity", "task manager", "brain dump", "focus", "adhd", "task tracking", "context switch", "task dashboard", "n8n", "workflow", "automation", "webhook", "integration", "ko-fi", "payment", "shop order"
+  - Load: `productivity/CONTEXT.md` (technology overview and patterns)
+  - Load: `productivity/troubleshooting.md` (error handling and debugging)
+  - If "n8n" mentioned: Load `productivity/n8n/CONTEXT.md` (n8n-specific documentation)
+  - If "ko-fi" mentioned: Load `productivity/n8n/workflows/kofi-paper-dynasty.md` (Ko-fi integration workflow)
+  - Note: ADHD-optimized task management with persistent terminal dashboard
+  - Note: Zero-friction brain dump capture to prevent context switching
+  - Note: n8n workflow automation platform at n8n.manticorum.com (LXC 210)
+  - Note: Ko-fi → Paper Dynasty integration for automated pack distribution
+  - Location: Task manager at `~/.claude/tools/task-manager/`, n8n at LXC 210 (10.10.0.210)
+
+**Media Server Keywords**
+- "jellyfin", "plex", "emby", "media server", "streaming", "watchstate", "watch history"
+  - Load: `media-servers/CONTEXT.md` (technology overview and patterns)
+  - If "jellyfin" mentioned: Load `media-servers/jellyfin-ubuntu-manticore.md` (Jellyfin-specific setup)
+  - Note: Jellyfin on ubuntu-manticore (10.10.0.226) with GPU transcoding
+  - Note: Shares GPU resources with Tdarr - coordinate concurrent usage
+
 ### Directory Context Triggers
 When working in specific directories:
 
-**Technology directories (/tdarr/, /docker/, /vm-management/, /networking/, /monitoring/)**
+**Technology directories (/tdarr/, /docker/, /vm-management/, /networking/, /monitoring/, /productivity/, /media-servers/)**
 - Load: `{technology}/CONTEXT.md` (technology overview)
 - Load: `{technology}/troubleshooting.md` (debugging info)
 
@@ -95,6 +114,7 @@ For troubleshooting scenarios, always load both context and troubleshooting file
   - If VM context detected: Load `vm-management/CONTEXT.md` AND `vm-management/troubleshooting.md`
   - If Network context detected: Load `networking/CONTEXT.md` AND `networking/troubleshooting.md`
   - If Monitoring context detected: Load `monitoring/CONTEXT.md` AND `monitoring/troubleshooting.md`
+  - If Productivity context detected: Load `productivity/CONTEXT.md` AND `productivity/troubleshooting.md`
 
 **Specific Tdarr Troubleshooting Keywords**
 - "forEach error", "staging timeout", "gaming detection", "plugin error", "container stop", "node disconnect", "cache cleanup", "shutdown tdarr", "stop tdarr", "emergency tdarr", "reset tdarr"
@@ -158,6 +178,15 @@ For troubleshooting scenarios, always load both context and troubleshooting file
       ├── CONTEXT.md       # Script-specific documentation
       └── windows-desktop/ # Windows reboot monitoring with Discord notifications
 
+/productivity/             # Task management and productivity tools
+  ├── CONTEXT.md           # Technology overview, patterns, best practices
+  ├── troubleshooting.md   # Error handling and debugging
+  └── [Tools installed at ~/.claude/tools/task-manager/]
+
+/media-servers/            # Media streaming services (Jellyfin, Plex)
+  ├── CONTEXT.md           # Technology overview, GPU transcoding patterns
+  └── jellyfin-ubuntu-manticore.md  # Jellyfin setup on ubuntu-manticore
+
 /development/              # Programming language patterns and tools
   ├── python-CONTEXT.md    # Python development patterns
   ├── nodejs-CONTEXT.md    # Node.js development patterns