diff --git a/cli.py b/cli.py
index 337da08a7e..55372bbb00 100644
--- a/cli.py
+++ b/cli.py
@@ -5244,9 +5244,33 @@ class HermesCLI:
                         context_length=ctx_len,
                     )
                 _cprint("  ✨ (◕‿◕)✨ Fresh start! Screen cleared and conversation reset.\n")
+                # Show a random tip on new session
+                try:
+                    from hermes_cli.tips import get_random_tip
+                    _tip = get_random_tip()
+                    try:
+                        from hermes_cli.skin_engine import get_active_skin
+                        _tip_color = get_active_skin().get_color("banner_dim", "#B8860B")
+                    except Exception:
+                        _tip_color = "#B8860B"
+                    cc.print(f"[dim {_tip_color}]✦ Tip: {_tip}[/]")
+                except Exception:
+                    pass
             else:
                 self.show_banner()
                 print("  ✨ (◕‿◕)✨ Fresh start! Screen cleared and conversation reset.\n")
+                # Show a random tip on new session
+                try:
+                    from hermes_cli.tips import get_random_tip
+                    _tip = get_random_tip()
+                    try:
+                        from hermes_cli.skin_engine import get_active_skin
+                        _tip_color = get_active_skin().get_color("banner_dim", "#B8860B")
+                    except Exception:
+                        _tip_color = "#B8860B"
+                    self.console.print(f"[dim {_tip_color}]✦ Tip: {_tip}[/]")
+                except Exception:
+                    pass
         elif canonical == "history":
             self.show_history()
         elif canonical == "title":
@@ -8075,6 +8099,17 @@ class HermesCLI:
             _welcome_text = "Welcome to Hermes Agent! Type your message or /help for commands."
             _welcome_color = "#FFF8DC"
         self.console.print(f"[{_welcome_color}]{_welcome_text}[/]")
+        # Show a random tip to help users discover features
+        try:
+            from hermes_cli.tips import get_random_tip
+            _tip = get_random_tip()
+            try:
+                _tip_color = _welcome_skin.get_color("banner_dim", "#B8860B")
+            except Exception:
+                _tip_color = "#B8860B"
+            self.console.print(f"[dim {_tip_color}]✦ Tip: {_tip}[/]")
+        except Exception:
+            pass  # Tips are non-critical — never break startup
         if self.preloaded_skills and not self._startup_skills_line_shown:
             skills_label = ", ".join(self.preloaded_skills)
             self.console.print(
diff --git a/gateway/run.py b/gateway/run.py
index a5876bc147..56573d58ae 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -3965,9 +3965,16 @@ class GatewayRunner:
         except Exception:
             pass
 
+        # Append a random tip to the reset message
+        try:
+            from hermes_cli.tips import get_random_tip
+            _tip_line = f"\n✦ Tip: {get_random_tip()}"
+        except Exception:
+            _tip_line = ""
+
         if session_info:
-            return f"{header}\n\n{session_info}"
-        return header
+            return f"{header}\n\n{session_info}{_tip_line}"
+        return f"{header}{_tip_line}"
     
     async def _handle_profile_command(self, event: MessageEvent) -> str:
         """Handle /profile — show active profile name and home directory."""
diff --git a/hermes_cli/tips.py b/hermes_cli/tips.py
new file mode 100644
index 0000000000..223d8d5402
--- /dev/null
+++ b/hermes_cli/tips.py
@@ -0,0 +1,280 @@
+"""Random tips shown at CLI session start to help users discover features."""
+
+import random
+from typing import Optional
+
+# ---------------------------------------------------------------------------
+# Tip corpus — ~200 one-liners covering slash commands, CLI flags, config,
+# keybindings, tools, gateway, skills, profiles, and workflow tricks.
+# ---------------------------------------------------------------------------
+
+TIPS = [
+    # --- Slash Commands ---
+    "/btw <question> asks a quick side question without tools or history — great for clarifications.",
+    "/background <prompt> runs a task in a separate session while your current one stays free.",
+    "/branch forks the current session so you can explore a different direction without losing progress.",
+    "/compress manually compresses conversation context when things get long.",
+    "/rollback lists filesystem checkpoints — restore files the agent modified to any prior state.",
+    "/rollback diff 2 previews what changed since checkpoint 2 without restoring anything.",
+    "/rollback 2 src/file.py restores a single file from a specific checkpoint.",
+    "/title \"my project\" names your session — resume it later with /resume or hermes -c.",
+    "/resume picks up where you left off in a previously named session.",
+    "/queue <prompt> queues a message for the next turn without interrupting the current one.",
+    "/undo removes the last user/assistant exchange from the conversation.",
+    "/retry resends your last message — useful when the agent's response wasn't quite right.",
+    "/verbose cycles tool progress display: off → new → all → verbose.",
+    "/reasoning high increases the model's thinking depth. /reasoning show displays the reasoning.",
+    "/fast toggles priority processing for faster API responses (provider-dependent).",
+    "/yolo skips all dangerous command approval prompts for the rest of the session.",
+    "/model lets you switch models mid-session — try /model sonnet or /model gpt-5.",
+    "/model --global changes your default model permanently.",
+    "/personality pirate sets a fun personality — 14 built-in options from kawaii to shakespeare.",
+    "/skin changes the CLI theme — try ares, mono, slate, poseidon, or charizard.",
+    "/statusbar toggles a persistent bar showing model, tokens, context fill %, cost, and duration.",
+    "/tools disable browser temporarily removes browser tools for the current session.",
+    "/browser connect attaches browser tools to your running Chrome instance via CDP.",
+    "/plugins lists installed plugins and their status.",
+    "/cron manages scheduled tasks — set up recurring prompts with delivery to any platform.",
+    "/reload-mcp hot-reloads MCP server configuration without restarting.",
+    "/usage shows token usage, cost breakdown, and session duration.",
+    "/insights shows usage analytics for the last 30 days.",
+    "/paste checks your clipboard for an image and attaches it to your next message.",
+    "/profile shows which profile is active and its home directory.",
+    "/config shows your current configuration at a glance.",
+    "/stop kills all running background processes spawned by the agent.",
+
+    # --- @ Context References ---
+    "@file:path/to/file.py injects file contents directly into your message.",
+    "@file:main.py:10-50 injects only lines 10-50 of a file.",
+    "@folder:src/ injects a directory tree listing.",
+    "@diff injects your unstaged git changes into the message.",
+    "@staged injects your staged git changes (git diff --staged).",
+    "@git:5 injects the last 5 commits with full patches.",
+    "@url:https://example.com fetches and injects a web page's content.",
+    "Typing @ triggers filesystem path completion — navigate to any file interactively.",
+    "Combine multiple references: \"Review @file:main.py and @file:test.py for consistency.\"",
+
+    # --- Keybindings ---
+    "Alt+Enter (or Ctrl+J) inserts a newline for multi-line input.",
+    "Ctrl+C interrupts the agent. Double-press within 2 seconds to force exit.",
+    "Ctrl+Z suspends Hermes to the background — run fg in your shell to resume.",
+    "Tab accepts auto-suggestion ghost text or autocompletes slash commands.",
+    "Type a new message while the agent is working to interrupt and redirect it.",
+    "Alt+V pastes an image from your clipboard into the conversation.",
+    "Pasting 5+ lines auto-saves to a file and inserts a compact reference instead.",
+
+    # --- CLI Flags ---
+    "hermes -c resumes your most recent CLI session. hermes -c \"project name\" resumes by title.",
+    "hermes -w creates an isolated git worktree — perfect for parallel agent workflows.",
+    "hermes -w -q \"Fix issue #42\" combines worktree isolation with a one-shot query.",
+    "hermes chat -t web,terminal enables only specific toolsets for a focused session.",
+    "hermes chat -s github-pr-workflow preloads a skill at launch.",
+    "hermes chat -q \"query\" runs a single non-interactive query and exits.",
+    "hermes chat --max-turns 200 overrides the default 90-iteration limit per turn.",
+    "hermes chat --checkpoints enables filesystem snapshots before every destructive file change.",
+    "hermes --yolo bypasses all dangerous command approval prompts for the entire session.",
+    "hermes chat --source telegram tags the session for filtering in hermes sessions list.",
+    "hermes -p work chat runs under a specific profile without changing your default.",
+
+    # --- CLI Subcommands ---
+    "hermes doctor --fix diagnoses and auto-repairs config and dependency issues.",
+    "hermes dump outputs a compact setup summary — great for bug reports.",
+    "hermes config set KEY VALUE auto-routes secrets to .env and everything else to config.yaml.",
+    "hermes config edit opens config.yaml in your default editor.",
+    "hermes config check scans for missing or stale configuration options.",
+    "hermes sessions browse opens an interactive session picker with search.",
+    "hermes sessions stats shows session counts by platform and database size.",
+    "hermes sessions prune --older-than 30 cleans up old sessions.",
+    "hermes skills search react --source skills-sh searches the skills.sh public directory.",
+    "hermes skills check scans installed hub skills for upstream updates.",
+    "hermes skills tap add myorg/skills-repo adds a custom GitHub skill source.",
+    "hermes skills snapshot export setup.json exports your skill configuration for backup or sharing.",
+    "hermes mcp add github --command npx adds MCP servers from the command line.",
+    "hermes mcp serve runs Hermes itself as an MCP server for other agents.",
+    "hermes auth add lets you add multiple API keys for credential pool rotation.",
+    "hermes completion bash >> ~/.bashrc enables tab completion for all commands and profiles.",
+    "hermes logs -f follows agent.log in real time. --level WARNING --since 1h filters output.",
+    "hermes backup creates a zip backup of your entire Hermes home directory.",
+    "hermes profile create coder creates an isolated profile that becomes its own command.",
+    "hermes profile create work --clone copies your current config and keys to a new profile.",
+    "hermes update syncs new bundled skills to ALL profiles automatically.",
+    "hermes gateway install sets up Hermes as a system service (systemd/launchd).",
+    "hermes memory setup lets you configure an external memory provider (Honcho, Mem0, etc.).",
+    "hermes webhook subscribe creates event-driven webhook routes with HMAC validation.",
+
+    # --- Configuration ---
+    "Set display.bell_on_complete: true in config.yaml to hear a bell when long tasks finish.",
+    "Set display.streaming: true to see tokens appear in real time as the model generates.",
+    "Set display.show_reasoning: true to watch the model's chain-of-thought reasoning.",
+    "Set display.compact: true to reduce whitespace in output for denser information.",
+    "Set display.busy_input_mode: queue to queue messages instead of interrupting the agent.",
+    "Set display.resume_display: minimal to skip the full conversation recap on session resume.",
+    "Set compression.threshold: 0.50 to control when auto-compression fires (default: 50% of context).",
+    "Set agent.max_turns: 200 to let the agent take more tool-calling steps per turn.",
+    "Set file_read_max_chars: 200000 to increase the max content per read_file call.",
+    "Set approvals.mode: smart to let an LLM auto-approve safe commands and auto-deny dangerous ones.",
+    "Set fallback_model in config.yaml to automatically fail over to a backup provider.",
+    "Set privacy.redact_pii: true to hash user IDs and phone numbers before sending to the LLM.",
+    "Set browser.record_sessions: true to auto-record browser sessions as WebM videos.",
+    "Set worktree: true in config.yaml to always create a git worktree (same as hermes -w).",
+    "Set security.website_blocklist.enabled: true to block specific domains from web tools.",
+    "Set cron.wrap_response: false to deliver raw agent output without the cron header/footer.",
+    "HERMES_TIMEZONE overrides the server timezone with any IANA timezone string.",
+    "Environment variable substitution works in config.yaml: use ${VAR_NAME} syntax.",
+    "Quick commands in config.yaml run shell commands instantly with zero token usage.",
+    "Custom personalities can be defined in config.yaml under agent.personalities.",
+    "provider_routing controls OpenRouter provider sorting, whitelisting, and blacklisting.",
+
+    # --- Tools & Capabilities ---
+    "execute_code runs Python scripts that call Hermes tools programmatically — results stay out of context.",
+    "delegate_task spawns up to 3 concurrent sub-agents with isolated contexts for parallel work.",
+    "web_extract works on PDF URLs — pass any PDF link and it converts to markdown.",
+    "search_files is ripgrep-backed and faster than grep — use it instead of terminal grep.",
+    "patch uses 9 fuzzy matching strategies so minor whitespace differences won't break edits.",
+    "patch supports V4A format for bulk multi-file edits in a single call.",
+    "read_file suggests similar filenames when a file isn't found.",
+    "read_file auto-deduplicates — re-reading an unchanged file returns a lightweight stub.",
+    "browser_vision takes a screenshot and analyzes it with AI — works for CAPTCHAs and visual content.",
+    "browser_console can evaluate JavaScript expressions in the page context.",
+    "image_generate creates images with FLUX 2 Pro and automatic 2x upscaling.",
+    "text_to_speech converts text to audio — plays as voice bubbles on Telegram.",
+    "send_message can reach any connected messaging platform from within a session.",
+    "The todo tool helps the agent track complex multi-step tasks during a session.",
+    "session_search performs full-text search across ALL past conversations.",
+    "The agent automatically saves preferences, corrections, and environment facts to memory.",
+    "mixture_of_agents routes hard problems through 4 frontier LLMs collaboratively.",
+    "Terminal commands support background mode with notify_on_complete for long-running tasks.",
+    "Terminal background processes support watch_patterns to alert on specific output lines.",
+    "The terminal tool supports 6 backends: local, Docker, SSH, Modal, Daytona, and Singularity.",
+
+    # --- Profiles ---
+    "Each profile gets its own config, API keys, memory, sessions, skills, and cron jobs.",
+    "Profile names become shell commands — 'hermes profile create coder' creates the 'coder' command.",
+    "hermes profile export coder -o backup.tar.gz creates a portable profile archive.",
+    "If two profiles accidentally share a bot token, the second gateway is blocked with a clear error.",
+
+    # --- Sessions ---
+    "Sessions auto-generate descriptive titles after the first exchange — no manual naming needed.",
+    "Session titles support lineage: \"my project\" → \"my project #2\" → \"my project #3\".",
+    "When exiting, Hermes prints a resume command with session ID and stats.",
+    "hermes sessions export backup.jsonl exports all sessions for backup or analysis.",
+    "hermes -r SESSION_ID resumes any specific past session by its ID.",
+
+    # --- Memory ---
+    "Memory is a frozen snapshot — changes appear in the system prompt only at next session start.",
+    "Memory entries are automatically scanned for prompt injection and exfiltration patterns.",
+    "The agent has two memory stores: personal notes (~2200 chars) and user profile (~1375 chars).",
+    "Corrections you give the agent (\"no, do it this way\") are often auto-saved to memory.",
+
+    # --- Skills ---
+    "Over 80 bundled skills covering github, creative, mlops, productivity, research, and more.",
+    "Every installed skill automatically becomes a slash command — type / to see them all.",
+    "hermes skills install official/security/1password installs optional skills from the repo.",
+    "Skills can restrict to specific OS platforms — some only load on macOS or Linux.",
+    "skills.external_dirs in config.yaml lets you load skills from custom directories.",
+    "The agent can create its own skills as procedural memory using skill_manage.",
+    "The plan skill saves markdown plans under .hermes/plans/ in the active workspace.",
+
+    # --- Cron & Scheduling ---
+    "Cron jobs can attach skills: hermes cron add --skill blogwatcher \"Check for new posts\".",
+    "Cron delivery targets include telegram, discord, slack, email, sms, and 12+ more platforms.",
+    "If a cron response starts with [SILENT], delivery is suppressed — useful for monitoring-only jobs.",
+    "Cron supports relative delays (30m), intervals (every 2h), cron expressions, and ISO timestamps.",
+    "Cron jobs run in completely fresh agent sessions — prompts must be self-contained.",
+
+    # --- Voice ---
+    "Voice mode works with zero API keys if faster-whisper is installed (free local speech-to-text).",
+    "Five TTS providers available: Edge TTS (free), ElevenLabs, OpenAI, NeuTTS (free local), MiniMax.",
+    "/voice on enables voice mode in the CLI. Ctrl+B toggles push-to-talk recording.",
+    "Streaming TTS plays sentences as they generate — you don't wait for the full response.",
+    "Voice messages on Telegram, Discord, WhatsApp, and Slack are auto-transcribed.",
+
+    # --- Gateway & Messaging ---
+    "Hermes runs on 18 platforms: Telegram, Discord, Slack, WhatsApp, Signal, Matrix, email, and more.",
+    "hermes gateway install sets it up as a system service that starts on boot.",
+    "DingTalk uses Stream Mode — no webhooks or public URL needed.",
+    "BlueBubbles brings iMessage to Hermes via a local macOS server.",
+    "Webhook routes support HMAC validation, rate limiting, and event filtering.",
+    "The API server exposes an OpenAI-compatible endpoint compatible with Open WebUI and LibreChat.",
+    "Discord voice channel mode: the bot joins VC, transcribes speech, and talks back.",
+    "group_sessions_per_user: true gives each person their own session in group chats.",
+    "/sethome marks a chat as the home channel for cron job deliveries.",
+    "The gateway supports inactivity-based timeouts — active agents can run indefinitely.",
+
+    # --- Security ---
+    "Dangerous command approval has 4 tiers: once, session, always (permanent allowlist), deny.",
+    "Smart approval mode uses an LLM to auto-approve safe commands and flag dangerous ones.",
+    "SSRF protection blocks private networks, loopback, link-local, and cloud metadata addresses.",
+    "Tirith pre-exec scanning detects homograph URL spoofing and pipe-to-interpreter patterns.",
+    "MCP subprocesses receive a filtered environment — only safe system vars pass through.",
+    "Context files (.hermes.md, AGENTS.md) are security-scanned for prompt injection before loading.",
+    "command_allowlist in config.yaml permanently approves specific shell command patterns.",
+
+    # --- Context & Compression ---
+    "Context auto-compresses when it reaches the threshold — memories are flushed and history summarized.",
+    "The status bar turns yellow, then orange, then red as context fills up.",
+    "SOUL.md at ~/.hermes/SOUL.md is the agent's primary identity — customize it to shape behavior.",
+    "Hermes loads project context from .hermes.md, AGENTS.md, CLAUDE.md, or .cursorrules (first match).",
+    "Subdirectory AGENTS.md files are discovered progressively as the agent navigates into folders.",
+    "Context files are capped at 20,000 characters with smart head/tail truncation.",
+
+    # --- Browser ---
+    "Five browser providers: local Chromium, Browserbase, Browser Use, Camofox, and Firecrawl.",
+    "Camofox is an anti-detection browser — Firefox fork with C++ fingerprint spoofing.",
+    "browser_navigate returns a page snapshot automatically — no need to call browser_snapshot after.",
+    "browser_vision with annotate=true overlays numbered labels on interactive elements.",
+
+    # --- MCP ---
+    "MCP servers are configured in config.yaml — both stdio and HTTP transports supported.",
+    "Per-server tool filtering: tools.include whitelists and tools.exclude blacklists specific tools.",
+    "MCP servers auto-generate toolsets at runtime — hermes tools can toggle them per platform.",
+    "MCP OAuth support: auth: oauth enables browser-based authorization with PKCE.",
+
+    # --- Checkpoints & Rollback ---
+    "Checkpoints have zero overhead when no files are modified — enabled by default.",
+    "A pre-rollback snapshot is saved automatically so you can undo the undo.",
+    "/rollback also undoes the conversation turn, so the agent doesn't remember rolled-back changes.",
+    "Checkpoints use shadow repos in ~/.hermes/checkpoints/ — your project's .git is never touched.",
+
+    # --- Batch & Data ---
+    "batch_runner.py processes hundreds of prompts in parallel for training data generation.",
+    "hermes chat -Q enables quiet mode for programmatic use — suppresses banner and spinner.",
+    "Trajectory saving (--save-trajectories) captures full tool-use traces for model training.",
+
+    # --- Plugins ---
+    "Three plugin types: general (tools/hooks), memory providers, and context engines.",
+    "hermes plugins install owner/repo installs plugins directly from GitHub.",
+    "8 external memory providers available: Honcho, OpenViking, Mem0, Hindsight, and more.",
+    "Plugin hooks include pre_tool_call, post_tool_call, pre_llm_call, and post_llm_call.",
+
+    # --- Miscellaneous ---
+    "Prompt caching (Anthropic) reduces costs by reusing cached system prompt prefixes.",
+    "The agent auto-generates session titles in a background thread — zero latency impact.",
+    "Smart model routing can auto-route simple queries to a cheaper model.",
+    "Slash commands support prefix matching: /h resolves to /help, /mod to /model.",
+    "Dragging a file path into the terminal auto-attaches images or sends as context.",
+    ".worktreeinclude in your repo root lists gitignored files to copy into worktrees.",
+    "hermes acp runs Hermes as an ACP server for VS Code, Zed, and JetBrains integration.",
+    "Custom providers: save named endpoints in config.yaml under custom_providers.",
+    "HERMES_EPHEMERAL_SYSTEM_PROMPT injects a system prompt that's never persisted to history.",
+    "credential_pool_strategies supports fill_first, round_robin, least_used, and random rotation.",
+    "hermes login supports OAuth-based auth for Nous and OpenAI Codex providers.",
+    "The API server supports both Chat Completions and Responses API with server-side state.",
+    "tool_preview_length: 0 in config shows full file paths in the spinner's activity feed.",
+    "hermes status --deep runs deeper diagnostic checks across all components.",
+]
+
+
+def get_random_tip(exclude_recent: int = 0) -> str:
+    """Return a random tip string.
+
+    Args:
+        exclude_recent: not used currently; reserved for future
+            deduplication across sessions.
+    """
+    return random.choice(TIPS)
+
+
+def get_tip_count() -> int:
+    """Return the total number of tips available."""
+    return len(TIPS)
diff --git a/tests/hermes_cli/test_tips.py b/tests/hermes_cli/test_tips.py
new file mode 100644
index 0000000000..88e00e0ce6
--- /dev/null
+++ b/tests/hermes_cli/test_tips.py
@@ -0,0 +1,77 @@
+"""Tests for hermes_cli/tips.py — random tip display at session start."""
+
+import pytest
+from hermes_cli.tips import TIPS, get_random_tip, get_tip_count
+
+
+class TestTipsCorpus:
+    """Validate the tip corpus itself."""
+
+    def test_has_at_least_200_tips(self):
+        assert len(TIPS) >= 200, f"Expected 200+ tips, got {len(TIPS)}"
+
+    def test_no_duplicates(self):
+        assert len(TIPS) == len(set(TIPS)), "Duplicate tips found"
+
+    def test_all_tips_are_strings(self):
+        for i, tip in enumerate(TIPS):
+            assert isinstance(tip, str), f"Tip {i} is not a string: {type(tip)}"
+
+    def test_no_empty_tips(self):
+        for i, tip in enumerate(TIPS):
+            assert tip.strip(), f"Tip {i} is empty or whitespace-only"
+
+    def test_max_length_reasonable(self):
+        """Tips should fit on a single terminal line (~120 chars max)."""
+        for i, tip in enumerate(TIPS):
+            assert len(tip) <= 150, (
+                f"Tip {i} too long ({len(tip)} chars): {tip[:60]}..."
+            )
+
+    def test_no_leading_trailing_whitespace(self):
+        for i, tip in enumerate(TIPS):
+            assert tip == tip.strip(), f"Tip {i} has leading/trailing whitespace"
+
+
+class TestGetRandomTip:
+    """Validate the get_random_tip() function."""
+
+    def test_returns_string(self):
+        tip = get_random_tip()
+        assert isinstance(tip, str)
+        assert len(tip) > 0
+
+    def test_returns_tip_from_corpus(self):
+        tip = get_random_tip()
+        assert tip in TIPS
+
+    def test_randomness(self):
+        """Multiple calls should eventually return different tips."""
+        seen = set()
+        for _ in range(50):
+            seen.add(get_random_tip())
+        # With 200+ tips and 50 draws, we should see at least 10 unique
+        assert len(seen) >= 10, f"Only got {len(seen)} unique tips in 50 draws"
+
+
+class TestGetTipCount:
+    def test_matches_corpus_length(self):
+        assert get_tip_count() == len(TIPS)
+
+
+class TestTipIntegrationInCLI:
+    """Test that the tip display code in cli.py works correctly."""
+
+    def test_tip_import_works(self):
+        """The import used in cli.py must succeed."""
+        from hermes_cli.tips import get_random_tip
+        assert callable(get_random_tip)
+
+    def test_tip_display_format(self):
+        """Verify the Rich markup format doesn't break."""
+        tip = get_random_tip()
+        color = "#B8860B"
+        markup = f"[dim {color}]✦ Tip: {tip}[/]"
+        # Should not contain nested/broken Rich tags
+        assert markup.count("[/]") == 1
+        assert "[dim #B8860B]" in markup