diff --git a/scripts/generate_cli_docs.py b/scripts/generate_cli_docs.py
index df46c6f..bfe538b 100644
--- a/scripts/generate_cli_docs.py
+++ b/scripts/generate_cli_docs.py
@@ -20,6 +20,7 @@
 sys.path.insert(0, str(Path(__file__).resolve().parent.parent / "src"))
 
 import click
+import typer.core
 import typer.main
 
 from social_hook.cli import app
@@ -30,6 +31,9 @@
 # Commands to exclude from docs (internal hooks)
 HIDDEN_COMMANDS = {"commit-hook", "git-hook", "narrative-capture"}
 
+_OPTION_TYPES = (click.Option, typer.core.TyperOption)
+_ARGUMENT_TYPES = (click.Argument, typer.core.TyperArgument)
+
 
 def get_click_app() -> click.Group:
     return typer.main.get_command(app)
@@ -76,7 +80,7 @@ def render_params(cmd: click.Command) -> str:
     skip = {"install_completion", "show_completion", "help", "ctx"}
 
     # Arguments
-    args = [p for p in cmd.params if isinstance(p, click.Argument)]
+    args = [p for p in cmd.params if isinstance(p, _ARGUMENT_TYPES)]
     if args:
         lines.append("**Arguments:**")
         lines.append("")
@@ -93,7 +97,7 @@ def render_params(cmd: click.Command) -> str:
         lines.append("")
 
     # Options
-    opts = [p for p in cmd.params if isinstance(p, click.Option) and p.name not in skip]
+    opts = [p for p in cmd.params if isinstance(p, _OPTION_TYPES) and p.name not in skip]
     if opts:
         lines.append("**Options:**")
         lines.append("")
diff --git a/site-docs/DOC_STATUS.md b/site-docs/DOC_STATUS.md
index 383d019..e0a0b4d 100644
--- a/site-docs/DOC_STATUS.md
+++ b/site-docs/DOC_STATUS.md
@@ -1,5 +1,5 @@
-<!-- last_run_commit: e0675da9f57694de2e6857eec0784bce5137b864 -->
-<!-- last_run_date: 2026-04-16 -->
+<!-- last_run_commit: 1afe4f10d28bede2e584ead914465ebe9279dcb9 -->
+<!-- last_run_date: 2026-07-08 -->
 
 # Documentation Status
 
@@ -96,16 +96,17 @@ Tracks coverage of external docs against the codebase. Used by the docs maintena
 
 | Check | Last passed | Notes |
 |-------|-------------|-------|
-| CLI docs are fresh (`generate_cli_docs.py` output matches committed) | 2026-04-16 | |
-| `mkdocs.yml` nav entries match files in `site-docs/cli/` | 2026-04-16 | |
-| OAuth env vars in config.md use OAuth 2.0 names (`X_CLIENT_ID`, not `CONSUMER_KEY`) | 2026-04-16 | |
-| `ruff check src/ tests/` passes | 2026-04-16 | |
-| `mypy src/social_hook/` has no new errors (only pre-existing library stub issues) | 2026-04-16 | 28 errors, all `import-untyped` or `no-any-return` pre-existing; fixed new `assignment` error in `brief.py` |
-| All CLI commands with poor/partial docstrings have been enriched | 2026-04-16 | 16 commands across 6 files enriched |
-| `pipeline.md` accurately describes the two-stage evaluation flow and targets path | 2026-04-16 | |
-| `narrative-arcs.md` uses `episode_tags` (not `episode_type`) and documents strategy-scoped arcs | 2026-04-16 | |
-| All interactive CLI commands (e.g., `credentials add`) have documented non-interactive equivalents for agent/CI use | 2026-04-16 | `credentials add --set`, all destructive commands have `--yes`; `setup` wizard → write config.yaml directly |
-| All CLI command groups have enriched group-level help text (not just terse labels) | 2026-04-16 | `project` and `journey` enriched this run; all 24 groups now have descriptive help |
+| CLI docs are fresh (`generate_cli_docs.py` output matches committed) | 2026-07-08 | Fixed Typer 0.26 compat — `TyperOption`/`TyperArgument` no longer inherit from Click classes |
+| `mkdocs.yml` nav entries match files in `site-docs/cli/` | 2026-07-08 | 24/24 |
+| OAuth env vars in config.md use OAuth 2.0 names (`X_CLIENT_ID`, not `CONSUMER_KEY`) | 2026-07-08 | |
+| `ruff check src/ tests/` passes | 2026-07-08 | |
+| `ruff format --check src/ tests/` passes | 2026-07-08 | |
+| `mypy src/social_hook/` has no new errors (only pre-existing library stub issues) | 2026-07-08 | 28 errors, all `import-untyped` or `no-any-return` pre-existing |
+| All CLI commands with poor/partial docstrings have been enriched | 2026-07-08 | |
+| `pipeline.md` accurately describes the two-stage evaluation flow and targets path | 2026-07-08 | |
+| `narrative-arcs.md` uses `episode_tags` (not `episode_type`) and documents strategy-scoped arcs | 2026-07-08 | |
+| All interactive CLI commands (e.g., `credentials add`) have documented non-interactive equivalents for agent/CI use | 2026-07-08 | `credentials add --set`, all destructive commands have `--yes`; `setup` wizard → write config.yaml directly |
+| All CLI command groups have enriched group-level help text (not just terse labels) | 2026-07-08 | All 24 groups + subgroups have descriptive help; `project intro` enriched this run |
 
 ## Backlog (waiting_approval)
 
diff --git a/site-docs/cli/arc.md b/site-docs/cli/arc.md
index d6e82cc..504631b 100644
--- a/site-docs/cli/arc.md
+++ b/site-docs/cli/arc.md
@@ -1,6 +1,6 @@
 # social-hook arc
 
-Manage narrative arcs.
+Manage narrative arcs. Arcs are multi-post storylines that group related content under a theme, giving your audience a coherent thread to follow across posts.
 
 ---
 
diff --git a/site-docs/cli/bot.md b/site-docs/cli/bot.md
index de2b1de..e9260a8 100644
--- a/site-docs/cli/bot.md
+++ b/site-docs/cli/bot.md
@@ -1,6 +1,6 @@
 # social-hook bot
 
-Bot daemon management.
+Start, stop, and check status of the Telegram/Discord bot daemon. The bot provides an interactive chat interface for reviewing drafts, approving posts, and managing the pipeline.
 
 ---
 
diff --git a/site-docs/cli/config.md b/site-docs/cli/config.md
index db771a0..65c14c0 100644
--- a/site-docs/cli/config.md
+++ b/site-docs/cli/config.md
@@ -1,6 +1,6 @@
 # social-hook config
 
-View and modify configuration.
+View and modify the Social Hook configuration. Read the full config as YAML, get individual values by dotted key path, or set scalar values without editing files directly.
 
 ---
 
diff --git a/site-docs/cli/decision.md b/site-docs/cli/decision.md
index 9b5141b..75f2fdc 100644
--- a/site-docs/cli/decision.md
+++ b/site-docs/cli/decision.md
@@ -1,6 +1,6 @@
 # social-hook decision
 
-Decision management.
+Manage evaluation decisions. Decisions record whether a commit was deemed post-worthy by the LLM evaluator. Use these commands to list, delete, retrigger, rewind, or batch-evaluate decisions.
 
 ---
 
diff --git a/site-docs/cli/draft.md b/site-docs/cli/draft.md
index 90b62d6..1c7e18c 100644
--- a/site-docs/cli/draft.md
+++ b/site-docs/cli/draft.md
@@ -1,6 +1,6 @@
 # social-hook draft
 
-Draft lifecycle management.
+Manage the full draft lifecycle. Approve, reject, schedule, edit, redraft, promote, and post drafts. Also manage media attachments and view draft details and change history.
 
 ---
 
diff --git a/site-docs/cli/index.md b/site-docs/cli/index.md
index 8e35199..f4f7e2a 100644
--- a/site-docs/cli/index.md
+++ b/site-docs/cli/index.md
@@ -21,23 +21,23 @@ These options can be placed before any command.
 |-------|-------------|
 | [`account`](account.md) | Manage OAuth-authenticated platform accounts (X, LinkedIn). |
 | [`advisory`](advisory.md) | Manage advisory items — operator action items for manual tasks. |
-| [`arc`](arc.md) | Manage narrative arcs. |
-| [`bot`](bot.md) | Bot daemon management. |
+| [`arc`](arc.md) | Manage narrative arcs. Arcs are multi-post storylines that group related content under a theme, giving your audience a coherent thread to follow across posts. |
+| [`bot`](bot.md) | Start, stop, and check status of the Telegram/Discord bot daemon. The bot provides an interactive chat interface for reviewing drafts, approving posts, and managing the pipeline. |
 | [`brief`](brief.md) | View and edit the project brief used by the evaluator and drafter. |
-| [`config`](config.md) | View and modify configuration. |
+| [`config`](config.md) | View and modify the Social Hook configuration. Read the full config as YAML, get individual values by dotted key path, or set scalar values without editing files directly. |
 | [`content`](content.md) | Submit content ideas, combine topics, and trigger hero launch drafts. |
 | [`credentials`](credentials.md) | Manage API keys and secrets in ~/.social-hook/.env. |
 | [`cycles`](cycles.md) | Inspect evaluation cycle history and per-strategy outcomes. |
-| [`decision`](decision.md) | Decision management. |
-| [`draft`](draft.md) | Draft lifecycle management. |
-| [`inspect`](inspect.md) | Inspect system state. |
+| [`decision`](decision.md) | Manage evaluation decisions. Decisions record whether a commit was deemed post-worthy by the LLM evaluator. Use these commands to list, delete, retrigger, rewind, or batch-evaluate decisions. |
+| [`draft`](draft.md) | Manage the full draft lifecycle. Approve, reject, schedule, edit, redraft, promote, and post drafts. Also manage media attachments and view draft details and change history. |
+| [`inspect`](inspect.md) | Inspect system state. View the event log, list pending drafts awaiting action, check LLM token usage, and see configured platform connections. |
 | [`journey`](journey.md) | Control Development Journey capture. When enabled, Claude Code hooks record session narratives that feed into the evaluation pipeline as rich development context. |
-| [`logs`](logs.md) | Log queries, tailing, and health. |
-| [`manual`](manual.md) | Manual operations. |
-| [`media`](media.md) | Media management. |
-| [`memory`](memory.md) | Manage voice memories. |
+| [`logs`](logs.md) | Query, tail, and manage log entries. View recent errors and warnings, follow live log output, clear old entries, and check overall system health across all pipeline components. |
+| [`manual`](manual.md) | Run pipeline steps manually. Evaluate a commit, create drafts from a decision, consolidate multiple decisions into one draft, or post an approved draft — bypassing the automated scheduler. |
+| [`media`](media.md) | Manage generated media assets. Run garbage collection to remove orphaned files from the media cache that are no longer referenced by any draft. |
+| [`memory`](memory.md) | Manage voice memories. Voice memories are persistent style and tone instructions that the LLM drafter uses when generating content, such as 'avoid jargon' or 'use first person plural'. |
 | [`project`](project.md) | Register and manage projects. A project links a git repository (or folder) to Social Hook so commits are evaluated, content is drafted, and briefs are maintained. |
-| [`snapshot`](snapshot.md) | DB snapshot management. |
+| [`snapshot`](snapshot.md) | Save, restore, and manage database snapshots. Snapshots let you bookmark the full system state and roll back if needed. A safety backup is created automatically before any restore or reset. |
 | [`strategy`](strategy.md) | View and customize content strategies (voice, audience, editorial rules). |
 | [`target`](target.md) | Configure where content is distributed (account + destination + strategy). |
 | [`topics`](topics.md) | Manage the prioritised content topic queue per strategy. |
@@ -55,7 +55,7 @@ These options can be placed before any command.
 | [`rate-limits`](root-commands.md#social-hook-rate-limits) | Show current rate limit status (daily cap, gap timer, queue, cost). |
 | [`scheduler-tick`](root-commands.md#social-hook-scheduler-tick) | Post scheduled drafts whose time has arrived and promote deferred drafts. |
 | [`setup`](root-commands.md#social-hook-setup) | Configure social-hook. |
-| [`test`](root-commands.md#social-hook-test) | Test commit evaluation. |
+| [`test`](root-commands.md#social-hook-test) | Dry-run commit evaluation with real LLM calls but no database writes. Tests whether the AI considers commits post-worthy, with options to save results as JSON (--output) and diff against a previous run for regression testing (--compare). |
 | [`trigger`](root-commands.md#social-hook-trigger) | Run the full evaluation-to-draft pipeline for a single commit. |
 | [`version`](root-commands.md#social-hook-version) | Show version information. |
 | [`web`](root-commands.md#social-hook-web) | Start the web dashboard for managing your social-hook workflow visually. |
diff --git a/site-docs/cli/inspect.md b/site-docs/cli/inspect.md
index 40ff3e8..84b464b 100644
--- a/site-docs/cli/inspect.md
+++ b/site-docs/cli/inspect.md
@@ -1,6 +1,6 @@
 # social-hook inspect
 
-Inspect system state.
+Inspect system state. View the event log, list pending drafts awaiting action, check LLM token usage, and see configured platform connections.
 
 ---
 
diff --git a/site-docs/cli/logs.md b/site-docs/cli/logs.md
index bf4c4e3..3e83b39 100644
--- a/site-docs/cli/logs.md
+++ b/site-docs/cli/logs.md
@@ -1,6 +1,6 @@
 # social-hook logs
 
-Log queries, tailing, and health.
+Query, tail, and manage log entries. View recent errors and warnings, follow live log output, clear old entries, and check overall system health across all pipeline components.
 
 **Group options:**
 
diff --git a/site-docs/cli/manual.md b/site-docs/cli/manual.md
index c77cccb..26d6c6c 100644
--- a/site-docs/cli/manual.md
+++ b/site-docs/cli/manual.md
@@ -1,6 +1,6 @@
 # social-hook manual
 
-Manual operations.
+Run pipeline steps manually. Evaluate a commit, create drafts from a decision, consolidate multiple decisions into one draft, or post an approved draft — bypassing the automated scheduler.
 
 ---
 
diff --git a/site-docs/cli/media.md b/site-docs/cli/media.md
index b0b1bd6..55ac480 100644
--- a/site-docs/cli/media.md
+++ b/site-docs/cli/media.md
@@ -1,6 +1,6 @@
 # social-hook media
 
-Media management.
+Manage generated media assets. Run garbage collection to remove orphaned files from the media cache that are no longer referenced by any draft.
 
 ---
 
diff --git a/site-docs/cli/memory.md b/site-docs/cli/memory.md
index e857b7d..489434c 100644
--- a/site-docs/cli/memory.md
+++ b/site-docs/cli/memory.md
@@ -1,6 +1,6 @@
 # social-hook memory
 
-Manage voice memories.
+Manage voice memories. Voice memories are persistent style and tone instructions that the LLM drafter uses when generating content, such as 'avoid jargon' or 'use first person plural'.
 
 ---
 
diff --git a/site-docs/cli/project.md b/site-docs/cli/project.md
index ad24469..d920c9d 100644
--- a/site-docs/cli/project.md
+++ b/site-docs/cli/project.md
@@ -73,7 +73,7 @@ Example: social-hook project install-hook /path/to/repo
 
 ### `social-hook project intro`
 
-Manage per-platform introduction status.
+Manage per-platform introduction status. Tracks whether a project has posted its first 'introduction' on each platform — the intro post establishes context before regular content begins. Use 'status' to see which platforms have been introduced, 'set' to mark a platform as introduced, and 'reset' to clear introduction state.
 
 **Options:**
 
diff --git a/site-docs/cli/root-commands.md b/site-docs/cli/root-commands.md
index 695e40a..99f41db 100644
--- a/site-docs/cli/root-commands.md
+++ b/site-docs/cli/root-commands.md
@@ -152,7 +152,7 @@ Configure social-hook.
 
 ### `social-hook test`
 
-Test commit evaluation.
+Dry-run commit evaluation with real LLM calls but no database writes. Tests whether the AI considers commits post-worthy, with options to save results as JSON (--output) and diff against a previous run for regression testing (--compare).
 
 **Options:**
 
diff --git a/site-docs/cli/snapshot.md b/site-docs/cli/snapshot.md
index 5ad19e9..56bc022 100644
--- a/site-docs/cli/snapshot.md
+++ b/site-docs/cli/snapshot.md
@@ -1,6 +1,6 @@
 # social-hook snapshot
 
-DB snapshot management.
+Save, restore, and manage database snapshots. Snapshots let you bookmark the full system state and roll back if needed. A safety backup is created automatically before any restore or reset.
 
 ---
 
diff --git a/src/social_hook/cli/__init__.py b/src/social_hook/cli/__init__.py
index 4f40f21..0c4ef7a 100644
--- a/src/social_hook/cli/__init__.py
+++ b/src/social_hook/cli/__init__.py
@@ -161,6 +161,10 @@ def help_cmd(
     import json as json_mod
 
     import click
+    import typer.core
+
+    _OPTION_TYPES = (click.Option, typer.core.TyperOption)
+    _ARGUMENT_TYPES = (click.Argument, typer.core.TyperArgument)
 
     click_app = typer.main.get_command(app)
     # Handle --json appearing after command path (forgiving flag placement)
@@ -190,7 +194,7 @@ def _cmd_to_dict(cmd, name=None):
 
         args = []
         for param in cmd.params:
-            if isinstance(param, click.Argument):
+            if isinstance(param, _ARGUMENT_TYPES):
                 args.append(
                     {
                         "name": param.name,
@@ -203,7 +207,7 @@ def _cmd_to_dict(cmd, name=None):
         opts = []
         skip_names = {"install_completion", "show_completion", "help", "ctx"}
         for param in cmd.params:
-            if isinstance(param, click.Option):
+            if isinstance(param, _OPTION_TYPES):
                 if param.name in skip_names:
                     continue
                 opt_info = {
@@ -260,7 +264,7 @@ def _resolve_command(parts):
             global_options = []
             skip_names = {"install_completion", "show_completion", "help", "ctx"}
             for param in click_app.params:
-                if isinstance(param, click.Option) and param.name not in skip_names:
+                if isinstance(param, _OPTION_TYPES) and param.name not in skip_names:
                     opt_info = {
                         "name": param.opts[0] if param.opts else f"--{param.name}",
                     }
@@ -298,8 +302,8 @@ def _resolve_command(parts):
             typer.echo(f"Error: {e}")
             raise typer.Exit(1) from None
     else:
-        help_ctx = click.Context(click_app, info_name=PROJECT_SLUG)
-        typer.echo(click_app.get_help(help_ctx))
+        help_ctx = click.Context(click_app, info_name=PROJECT_SLUG)  # type: ignore[arg-type]
+        typer.echo(click_app.get_help(help_ctx))  # type: ignore[arg-type]
 
 
 @app.command()
@@ -527,7 +531,11 @@ def _kill_port(p: int) -> None:
 # Bot subcommand group
 # =============================================================================
 
-bot_app = typer.Typer(name="bot", help="Bot daemon management.", no_args_is_help=True)
+bot_app = typer.Typer(
+    name="bot",
+    help="Start, stop, and check status of the Telegram/Discord bot daemon. The bot provides an interactive chat interface for reviewing drafts, approving posts, and managing the pipeline.",
+    no_args_is_help=True,
+)
 app.add_typer(bot_app, name="bot")
 
 
@@ -970,16 +978,33 @@ def narrative_capture():
 )
 
 # Inspection commands: log, pending, usage
-app.add_typer(inspect_app, name="inspect", help="Inspect system state.")
+app.add_typer(
+    inspect_app,
+    name="inspect",
+    help="Inspect system state. View the event log, list pending drafts awaiting action, check LLM token usage, and see configured platform connections.",
+)
 
 # Manual commands: evaluate, draft, post
-app.add_typer(manual_app, name="manual", help="Manual operations.")
+app.add_typer(
+    manual_app,
+    name="manual",
+    help="Run pipeline steps manually. Evaluate a commit, create drafts from a decision, consolidate multiple decisions into one draft, or post an approved draft — bypassing the automated scheduler.",
+)
 
 # Setup wizard
 app.add_typer(setup_app, name="setup", help=f"Configure {PROJECT_SLUG}.")
 
 # Test command
-app.add_typer(test_app, name="test", help="Test commit evaluation.")
+app.add_typer(
+    test_app,
+    name="test",
+    help=(
+        "Dry-run commit evaluation with real LLM calls but no database writes. "
+        "Tests whether the AI considers commits post-worthy, with options to save "
+        "results as JSON (--output) and diff against a previous run for regression "
+        "testing (--compare)."
+    ),
+)
 
 # Journey capture commands: on, off, status
 app.add_typer(
@@ -989,32 +1014,60 @@ def narrative_capture():
 )
 
 # Config commands: show, get, set
-app.add_typer(config_app, name="config", help="View and modify configuration.")
+app.add_typer(
+    config_app,
+    name="config",
+    help="View and modify the Social Hook configuration. Read the full config as YAML, get individual values by dotted key path, or set scalar values without editing files directly.",
+)
 
 # Memory commands: list, add, delete, clear
-app.add_typer(memory_app, name="memory", help="Manage voice memories.")
+app.add_typer(
+    memory_app,
+    name="memory",
+    help="Manage voice memories. Voice memories are persistent style and tone instructions that the LLM drafter uses when generating content, such as 'avoid jargon' or 'use first person plural'.",
+)
 
 # Arc commands: list, create, complete, abandon
-app.add_typer(arc_app, name="arc", help="Manage narrative arcs.")
+app.add_typer(
+    arc_app,
+    name="arc",
+    help="Manage narrative arcs. Arcs are multi-post storylines that group related content under a theme, giving your audience a coherent thread to follow across posts.",
+)
 
 from social_hook.cli.decision import app as decision_app
 from social_hook.cli.draft import app as draft_app
 
-# Decision management: list, delete
-app.add_typer(decision_app, name="decision", help="Decision management.")
+# Decision management: list, delete, retrigger, rewind, batch-evaluate
+app.add_typer(
+    decision_app,
+    name="decision",
+    help="Manage evaluation decisions. Decisions record whether a commit was deemed post-worthy by the LLM evaluator. Use these commands to list, delete, retrigger, rewind, or batch-evaluate decisions.",
+)
 
 # Draft lifecycle: approve, reject, schedule, cancel, retry, edit, etc.
-app.add_typer(draft_app, name="draft", help="Draft lifecycle management.")
+app.add_typer(
+    draft_app,
+    name="draft",
+    help="Manage the full draft lifecycle. Approve, reject, schedule, edit, redraft, promote, and post drafts. Also manage media attachments and view draft details and change history.",
+)
 
 from social_hook.cli.media import app as media_app
 
 # Media commands: gc
-app.add_typer(media_app, name="media", help="Media management.")
+app.add_typer(
+    media_app,
+    name="media",
+    help="Manage generated media assets. Run garbage collection to remove orphaned files from the media cache that are no longer referenced by any draft.",
+)
 
 from social_hook.cli.snapshot import app as snapshot_app
 
 # DB snapshot management: save, restore, reset, list, delete
-app.add_typer(snapshot_app, name="snapshot", help="DB snapshot management.")
+app.add_typer(
+    snapshot_app,
+    name="snapshot",
+    help="Save, restore, and manage database snapshots. Snapshots let you bookmark the full system state and roll back if needed. A safety backup is created automatically before any restore or reset.",
+)
 
 from social_hook.cli.account import app as account_app
 from social_hook.cli.advisory import app as advisory_app
@@ -1091,7 +1144,11 @@ def narrative_capture():
 )
 
 # Log queries, tailing, and health
-app.add_typer(logs_app, name="logs", help="Log queries, tailing, and health.")
+app.add_typer(
+    logs_app,
+    name="logs",
+    help="Query, tail, and manage log entries. View recent errors and warnings, follow live log output, clear old entries, and check overall system health across all pipeline components.",
+)
 
 from social_hook.cli.events import events as events_cmd
 from social_hook.cli.quickstart import quickstart as quickstart_cmd
diff --git a/src/social_hook/cli/arc.py b/src/social_hook/cli/arc.py
index 933c49f..0b5284a 100644
--- a/src/social_hook/cli/arc.py
+++ b/src/social_hook/cli/arc.py
@@ -4,7 +4,10 @@
 
 import typer
 
-app = typer.Typer(no_args_is_help=True)
+app = typer.Typer(
+    no_args_is_help=True,
+    help="Manage narrative arcs. Arcs are multi-post storylines that group related content under a theme, giving your audience a coherent thread to follow across posts.",
+)
 
 
 def _resolve_project(project: str | None = None) -> str:
diff --git a/src/social_hook/cli/config.py b/src/social_hook/cli/config.py
index a38aacf..6a5748f 100644
--- a/src/social_hook/cli/config.py
+++ b/src/social_hook/cli/config.py
@@ -5,7 +5,10 @@
 import typer
 import yaml
 
-app = typer.Typer(no_args_is_help=True)
+app = typer.Typer(
+    no_args_is_help=True,
+    help="View and modify the Social Hook configuration. Read the full config as YAML, get individual values by dotted key path, or set scalar values without editing files directly.",
+)
 
 
 def _parse_value(value: str):
diff --git a/src/social_hook/cli/decision.py b/src/social_hook/cli/decision.py
index b7a8368..5fbcf88 100644
--- a/src/social_hook/cli/decision.py
+++ b/src/social_hook/cli/decision.py
@@ -7,7 +7,10 @@
 
 import typer
 
-app = typer.Typer(no_args_is_help=True)
+app = typer.Typer(
+    no_args_is_help=True,
+    help="Manage evaluation decisions. Decisions record whether a commit was deemed post-worthy by the LLM evaluator. Use these commands to list, delete, retrigger, rewind, or batch-evaluate decisions.",
+)
 
 
 def _get_conn():
diff --git a/src/social_hook/cli/draft.py b/src/social_hook/cli/draft.py
index 62792ab..d7c3c4f 100644
--- a/src/social_hook/cli/draft.py
+++ b/src/social_hook/cli/draft.py
@@ -9,7 +9,10 @@
 
 from social_hook.models.enums import PENDING_STATUSES, TERMINAL_STATUSES
 
-app = typer.Typer(no_args_is_help=True)
+app = typer.Typer(
+    no_args_is_help=True,
+    help="Manage the full draft lifecycle. Approve, reject, schedule, edit, redraft, promote, and post drafts. Also manage media attachments and view draft details and change history.",
+)
 
 
 def _get_conn():
diff --git a/src/social_hook/cli/inspect.py b/src/social_hook/cli/inspect.py
index 267a59d..23d13cc 100644
--- a/src/social_hook/cli/inspect.py
+++ b/src/social_hook/cli/inspect.py
@@ -2,7 +2,9 @@
 
 import typer
 
-app = typer.Typer()
+app = typer.Typer(
+    help="Inspect system state. View the event log, list pending drafts awaiting action, check LLM token usage, and see configured platform connections."
+)
 
 
 @app.command()
diff --git a/src/social_hook/cli/logs.py b/src/social_hook/cli/logs.py
index 89587ea..84ce775 100644
--- a/src/social_hook/cli/logs.py
+++ b/src/social_hook/cli/logs.py
@@ -6,7 +6,10 @@
 
 import typer
 
-app = typer.Typer(invoke_without_command=True)
+app = typer.Typer(
+    invoke_without_command=True,
+    help="Query, tail, and manage log entries. View recent errors and warnings, follow live log output, clear old entries, and check overall system health across all pipeline components.",
+)
 
 VALID_LOG_COMPONENTS = (
     "trigger",
diff --git a/src/social_hook/cli/manual.py b/src/social_hook/cli/manual.py
index 9e895d2..39288d5 100644
--- a/src/social_hook/cli/manual.py
+++ b/src/social_hook/cli/manual.py
@@ -4,7 +4,9 @@
 
 from social_hook.models.enums import PENDING_STATUSES
 
-app = typer.Typer()
+app = typer.Typer(
+    help="Run pipeline steps manually. Evaluate a commit, create drafts from a decision, consolidate multiple decisions into one draft, or post an approved draft — bypassing the automated scheduler.",
+)
 
 
 @app.command()
diff --git a/src/social_hook/cli/media.py b/src/social_hook/cli/media.py
index d5d7a3f..77aa7fb 100644
--- a/src/social_hook/cli/media.py
+++ b/src/social_hook/cli/media.py
@@ -4,7 +4,11 @@
 
 import typer
 
-app = typer.Typer(name="media", help="Media management.", no_args_is_help=True)
+app = typer.Typer(
+    name="media",
+    help="Manage generated media assets. Run garbage collection to remove orphaned files from the media cache that are no longer referenced by any draft.",
+    no_args_is_help=True,
+)
 
 
 @app.command("gc")
diff --git a/src/social_hook/cli/memory.py b/src/social_hook/cli/memory.py
index 2e515b9..ff2bc56 100644
--- a/src/social_hook/cli/memory.py
+++ b/src/social_hook/cli/memory.py
@@ -4,7 +4,10 @@
 
 import typer
 
-app = typer.Typer(no_args_is_help=True)
+app = typer.Typer(
+    no_args_is_help=True,
+    help="Manage voice memories. Voice memories are persistent style and tone instructions that the LLM drafter uses when generating content, such as 'avoid jargon' or 'use first person plural'.",
+)
 
 
 def _resolve_project(project: str | None = None) -> str:
diff --git a/src/social_hook/cli/project.py b/src/social_hook/cli/project.py
index 4dd0d78..f05f538 100644
--- a/src/social_hook/cli/project.py
+++ b/src/social_hook/cli/project.py
@@ -9,7 +9,9 @@
 app = typer.Typer(
     help="Register and manage projects. A project links a git repository (or folder) to Social Hook so commits are evaluated, content is drafted, and briefs are maintained."
 )
-intro_app = typer.Typer(help="Manage per-platform introduction status.")
+intro_app = typer.Typer(
+    help="Manage per-platform introduction status. Tracks whether a project has posted its first 'introduction' on each platform — the intro post establishes context before regular content begins. Use 'status' to see which platforms have been introduced, 'set' to mark a platform as introduced, and 'reset' to clear introduction state."
+)
 app.add_typer(intro_app, name="intro")
 prompt_docs_app = typer.Typer(help="Manage project prompt documentation files.")
 app.add_typer(prompt_docs_app, name="prompt-docs")
diff --git a/src/social_hook/cli/snapshot.py b/src/social_hook/cli/snapshot.py
index d2dd865..d6f6455 100644
--- a/src/social_hook/cli/snapshot.py
+++ b/src/social_hook/cli/snapshot.py
@@ -8,7 +8,10 @@
 
 import typer
 
-app = typer.Typer(no_args_is_help=True)
+app = typer.Typer(
+    no_args_is_help=True,
+    help="Save, restore, and manage database snapshots. Snapshots let you bookmark the full system state and roll back if needed. A safety backup is created automatically before any restore or reset.",
+)
 
 _NAME_RE = re.compile(r"^[a-zA-Z0-9_-]+$")
 _MAX_NAME_LEN = 64
diff --git a/tests/test_quickstart.py b/tests/test_quickstart.py
index 027b276..1520627 100644
--- a/tests/test_quickstart.py
+++ b/tests/test_quickstart.py
@@ -8,6 +8,7 @@
 
 import click
 import pytest
+import typer
 from typer.testing import CliRunner
 
 from social_hook.cli.quickstart import (
@@ -65,12 +66,12 @@ def mock_project():
 
 class TestErrorExit:
     def test_error_exit_text(self, capsys):
-        with pytest.raises(click.exceptions.Exit):
+        with pytest.raises((click.exceptions.Exit, typer.Exit)):
             _error_exit("something broke", is_json=False)
         assert "Error: something broke" in capsys.readouterr().err
 
     def test_error_exit_json(self, capsys):
-        with pytest.raises(click.exceptions.Exit):
+        with pytest.raises((click.exceptions.Exit, typer.Exit)):
             _error_exit("something broke", is_json=True)
         out = capsys.readouterr().out
         data = json.loads(out)
@@ -137,7 +138,7 @@ def test_auto_configure_no_provider_exits(self, temp_dir):
                 "social_hook.setup.wizard.discover_providers",
                 return_value=providers,
             ),
-            pytest.raises(click.exceptions.Exit),
+            pytest.raises((click.exceptions.Exit, typer.Exit)),
         ):
             _auto_configure(
                 temp_dir, api_key=None, strategies=["building-public"], is_json=True, verbose=False