feat(cli): Agent Mode bootstrap + claim flow (Python + Node) (#5123)

cli/python/pyproject.toml

@@ -4,7 +4,7 @@ build-backend = "hatchling.build"
 
 [project]
 name = "mem0-cli"
-version = "0.2.4"
+version = "0.2.5"
 description = "The official CLI for mem0 — the memory layer for AI agents"
 readme = "README.md"
 license = "Apache-2.0"

cli/python/src/mem0_cli/agent_detect.py

@@ -0,0 +1,36 @@
+"""Detect whether the CLI is being invoked from inside an AI-agent context.
+
+Used by `mem0 init` to auto-enter Agent Mode (Rule 3 bootstrap) when an
+agent runtime env var is present. The return value is a context **trigger
+only** — the canonical agent identity is self-declared by the agent via
+``--agent-caller <name>`` (Proof Editor-style) and never sniffed from env
+vars to fill the ``agent_caller`` field on the APIKey row.
+
+Returns a short name or None. The list is curated, not exhaustive — env
+vars we don't recognise fall through to None (caller treated as
+non-agent). Honest reporting depends on ``--agent-caller``; this list is
+just enough to enable the zero-friction auto-bootstrap UX.
+"""
+
+from __future__ import annotations
+
+import os
+
+_AGENT_CALLER_ENV: tuple[tuple[str, tuple[str, ...]], ...] = (
+    ("claude-code", ("CLAUDECODE", "CLAUDE_CODE")),
+    ("cursor", ("CURSOR_AGENT", "CURSOR_SESSION_ID")),
+    ("codex", ("CODEX_CLI", "OPENAI_CODEX")),
+    ("cline", ("CLINE_AGENT", "CLINE")),
+    ("continue", ("CONTINUE_AGENT", "CONTINUE_SESSION")),
+    ("aider", ("AIDER_SESSION",)),
+    ("goose", ("GOOSE_AGENT",)),
+    ("windsurf", ("WINDSURF_AGENT",)),
+)
+
+
+def detect_agent_caller() -> str | None:
+    """Return a canonical agent name if any agent env var is set, else None."""
+    for name, env_vars in _AGENT_CALLER_ENV:
+        if any(os.environ.get(v) for v in env_vars):
+            return name
+    return None

cli/python/src/mem0_cli/app.py

@@ -237,6 +237,14 @@ def main_callback(
         cmd_version()
         raise typer.Exit()
     if ctx.invoked_subcommand:
+        # Stash the active subcommand name so the JSON error envelope
+        # (print_error in agent mode) can report which command failed
+        # instead of an empty `"command": ""` field.
+        from mem0_cli.state import set_current_command
+
+        set_current_command(ctx.invoked_subcommand)
+    if ctx.invoked_subcommand and ctx.invoked_subcommand != "init":
+        # init fires its own telemetry from init_cmd.run_init with full M1-M6 props.
         _fire_telemetry(ctx.invoked_subcommand)
 
 
@@ -851,6 +859,19 @@ def init(
     force: bool = typer.Option(
         False, "--force", help="Overwrite existing config without confirmation."
     ),
+    agent_signal: bool = typer.Option(
+        False, "--agent", help="Bootstrap an unattended Agent Mode account (no email required)."
+    ),
+    source: str | None = typer.Option(
+        None,
+        "--source",
+        help="Channel attribution for signup (e.g. github, hn, ph).",
+    ),
+    agent_caller: str | None = typer.Option(
+        None,
+        "--agent-caller",
+        help="Self-declared agent identity (e.g. claude-code, cursor). Used with --agent to attribute Agent Mode signups.",
+    ),
 ) -> None:
     """Interactive setup wizard for mem0 CLI.
 
@@ -859,10 +880,38 @@ def init(
       mem0 init --api-key m0-xxx --user-id alice
       mem0 init --email alice@company.com
       mem0 init --email alice@company.com --code 482901
+      mem0 init --agent --agent-caller claude-code   # AI agent self-identifies on Agent Mode bootstrap
+      mem0 init --email alice@company.com  # Claims an existing Agent Mode key when one is present
     """
     from mem0_cli.commands.init_cmd import run_init
 
-    run_init(api_key=api_key, user_id=user_id, email=email, code=code, force=force)
+    run_init(
+        api_key=api_key,
+        user_id=user_id,
+        email=email,
+        code=code,
+        force=force,
+        source=source,
+        agent=agent_signal,
+        agent_caller=agent_caller,
+    )
+
+
+@app.command(rich_help_panel="Setup")
+def identify(
+    name: str = typer.Argument(..., help="Agent identity (e.g. claude-code, cursor, my-bot)."),
+) -> None:
+    """Tag your active Agent Mode key with the AI agent that's using it.
+
+    Run this once after `mem0 init --agent` if you didn't pass --agent-caller.
+    Idempotent — re-running just overwrites the value.
+
+    Example:
+      mem0 identify claude-code
+    """
+    from mem0_cli.commands.identify_cmd import run_identify
+
+    run_identify(name)
 
 
 # (entity_app registered at module level, below sub-group definitions)
@@ -1198,11 +1247,28 @@ def main() -> None:
     import sys
 
     # Allow --json/--agent anywhere in the command line (not just before subcommand).
-    _json_flags = {"--json", "--agent"}
-    if any(a in _json_flags for a in sys.argv[1:]):
+    # Special case: `mem0 init --agent` is a subcommand flag (Agent Mode bootstrap)
+    # consumed by init_cmd, not a global JSON-output toggle — leave it in argv.
+    argv_rest = sys.argv[1:]
+    is_init = "init" in argv_rest
+    _global_flags = {"--json"} if is_init else {"--json", "--agent"}
+    if any(a in _global_flags for a in argv_rest):
         from mem0_cli.state import set_agent_mode
 
         set_agent_mode(True)
-        sys.argv = [sys.argv[0]] + [a for a in sys.argv[1:] if a not in _json_flags]
+        sys.argv = [sys.argv[0]] + [a for a in argv_rest if a not in _global_flags]
 
-    app()
+    try:
+        app()
+    finally:
+        # Surface any unclaimed Agent Mode notice once per command, after the
+        # primary output. In JSON/agent mode the notice is folded into the
+        # envelope by format_json_envelope, so skip the stderr banner there
+        # to avoid duplicate output.
+        from mem0_cli.state import is_agent_mode, take_notice
+
+        notice = take_notice()
+        if notice and not is_agent_mode():
+            from rich.console import Console
+
+            Console(stderr=True).print(f"\n[yellow]🔔 {notice}[/yellow]\n")

cli/python/src/mem0_cli/backend/platform.py

@@ -30,7 +30,7 @@ class PlatformBackend(Backend):
         )
 
     def _request(self, method: str, path: str, **kwargs: Any) -> Any:
-        from mem0_cli.state import is_agent_mode
+        from mem0_cli.state import capture_notice, is_agent_mode
 
         self._client.headers["X-Mem0-Caller-Type"] = "agent" if is_agent_mode() else "user"
         resp = self._client.request(method, path, **kwargs)
@@ -48,7 +48,26 @@ class PlatformBackend(Backend):
         resp.raise_for_status()
         if resp.status_code == 204:
             return {}
-        return resp.json()
+        data = resp.json()
+
+        # Pull the unclaimed-Agent-Mode notice out of the body (or the header
+        # fallback for endpoints that return non-dict / non-dict-leading
+        # payloads) and stash it for end-of-command surfacing.
+        notice = None
+        if isinstance(data, dict) and "mem0_notice" in data:
+            notice = data.pop("mem0_notice")
+        elif (
+            isinstance(data, list)
+            and data
+            and isinstance(data[0], dict)
+            and "mem0_notice" in data[0]
+        ):
+            notice = data[0].pop("mem0_notice")
+        if notice is None:
+            notice = resp.headers.get("X-Mem0-Notice-Message") or None
+        capture_notice(notice)
+
+        return data
 
     def add(
         self,

cli/python/src/mem0_cli/branding.py

@@ -87,10 +87,12 @@ def print_error(console: Console, message: str, hint: str | None = None) -> None
         }
         print(_json.dumps(envelope))
         return
+    from rich.markup import escape
+
     sym = _sym("✗", "[error]")
-    console.print(f"[{ERROR_COLOR}]{sym} Error:[/] {message}")
+    console.print(f"[{ERROR_COLOR}]{sym} Error:[/] {escape(str(message))}")
     if hint:
-        console.print(f"  [{DIM_COLOR}]{hint}[/]")
+        console.print(f"  [{DIM_COLOR}]{escape(str(hint))}[/]")
 
 
 def print_warning(console: Console, message: str) -> None:

cli/python/src/mem0_cli/commands/agent_mode_cmd.py

@@ -0,0 +1,239 @@
+"""Agent Mode commands — bootstrap (unattended signup) and claim (OTP-based human upgrade)."""
+
+from __future__ import annotations
+
+import json
+import sys
+from datetime import datetime, timezone
+from typing import Any
+
+import httpx
+import typer
+from rich.console import Console
+from rich.prompt import Prompt
+
+from mem0_cli.branding import (
+    BRAND_COLOR,
+    DIM_COLOR,
+    print_error,
+    print_success,
+)
+from mem0_cli.config import Mem0Config, save_config
+
+console = Console()
+err_console = Console(stderr=True)
+
+_SOURCE_HEADERS = {
+    "X-Mem0-Source": "cli",
+    "X-Mem0-Client-Language": "python",
+}
+
+
+def _validate_envelope(envelope: Any) -> None:
+    """Defend against partial/malformed backend responses.
+
+    A backend regression that returns ``{"api_key": null}`` would otherwise be
+    silently persisted, producing confusing downstream errors far from the
+    source. Fail fast with a clear message if the required fields are missing.
+    """
+    if not isinstance(envelope, dict):
+        print_error(err_console, "Bootstrap response was not a JSON object.")
+        raise typer.Exit(1)
+    for field in ("api_key", "default_user_id"):
+        value = envelope.get(field)
+        if not isinstance(value, str) or not value:
+            print_error(
+                err_console,
+                f"Bootstrap response missing required field {field!r} — please update the CLI.",
+            )
+            raise typer.Exit(1)
+
+
+def bootstrap_via_backend(
+    config: Mem0Config,
+    *,
+    source: str | None = None,
+    agent_caller: str | None = None,
+) -> None:
+    """POST /api/v1/auth/agent_mode/ and mutate config in place.
+
+    Args:
+        config: Mem0Config mutated in place with the new platform values.
+        source: ``--source`` flag passthrough (analytics tag, free-form).
+        agent_caller: Self-declared agent identity passed via ``--agent-caller``
+            (e.g. ``claude-code``, ``cursor``). May be None when the caller
+            omitted the flag; the agent can backfill later via
+            ``mem0 identify <name>``. Sent to the backend in the request body
+            and saved into ``platform.agent_caller`` for local introspection.
+
+    Raises typer.Exit(1) on failure.
+    """
+    base_url = (config.platform.base_url or "https://api.mem0.ai").rstrip("/")
+    body: dict[str, Any] = {}
+    if source:
+        body["source"] = source
+    if agent_caller:
+        body["agent_caller"] = agent_caller
+
+    try:
+        with httpx.Client(timeout=30.0) as client:
+            resp = client.post(
+                f"{base_url}/api/v1/auth/agent_mode/",
+                headers={**_SOURCE_HEADERS, "Content-Type": "application/json"},
+                json=body,
+            )
+    except httpx.HTTPError as exc:
+        print_error(err_console, f"Network error contacting Mem0: {exc}")
+        raise typer.Exit(1) from exc
+
+    if resp.status_code == 429:
+        print_error(err_console, "Rate-limited. Try again in a few minutes.")
+        raise typer.Exit(1)
+    if resp.status_code == 503:
+        print_error(err_console, "Agent Mode is temporarily disabled. Try again later.")
+        raise typer.Exit(1)
+    if resp.status_code != 200:
+        detail = resp.text
+        try:
+            err_body = resp.json()
+            detail = err_body.get("error") or err_body.get("detail") or resp.text
+        except (json.JSONDecodeError, ValueError, AttributeError):
+            pass
+        # Backend's @ratelimit decorator raises PermissionDenied, which DRF
+        # translates to a generic 403 "You do not have permission to perform
+        # this action." That's opaque — surface as the rate-limit it actually is.
+        if resp.status_code == 403 and "permission" in str(detail).lower():
+            print_error(
+                err_console,
+                "Daily Agent Mode signup limit reached for this network (5/day). Try again from a different IP or after midnight UTC.",
+            )
+            raise typer.Exit(1)
+        print_error(err_console, f"Bootstrap failed: {detail}")
+        raise typer.Exit(1)
+
+    envelope = resp.json()
+    _validate_envelope(envelope)
+    config.platform.api_key = envelope["api_key"]
+    config.platform.base_url = base_url
+    config.platform.agent_mode = True
+    config.platform.created_via = "agent_mode"
+    config.platform.agent_caller = agent_caller or ""
+    config.platform.claimed_at = ""
+    config.platform.default_user_id = envelope["default_user_id"]
+    # Adopt the slug-derived user_id as the default scope for memory ops.
+    config.defaults.user_id = envelope["default_user_id"]
+    save_config(config)
+
+    print_success(console, f"Agent Mode active. Default user_id: {envelope['default_user_id']}")
+    notice = envelope.get("mem0_notice")
+    if notice:
+        console.print(f"\n[yellow]🔔 {notice}[/yellow]\n")
+    else:
+        # Fallback if the backend hasn't deployed the unified notice yet.
+        claim_cmd = envelope.get("claim_command", "mem0 init --email <your-email>")
+        console.print(f"  [{DIM_COLOR}]To claim this account later: {claim_cmd}[/]")
+
+    if not agent_caller:
+        console.print(
+            f"  [{DIM_COLOR}]If you are an AI agent, identify yourself: "
+            f"`mem0 identify <your-name>` (e.g. claude-code, cursor).[/]"
+        )
+
+
+def claim_via_otp(config: Mem0Config, *, email: str, code: str | None = None) -> None:
+    """Claim an existing Agent Mode account via OTP — no browser, no polling.
+
+    Reuses the standard email-code flow (`/api/v1/auth/email_code/` then
+    `/.../verify/`) and adds the local agent-mode API key in the verify body
+    as `agent_mode_api_key`. Backend's `verify_email_code` runs the
+    upgrade-in-place transaction inline and returns claim result.
+
+    On success: flips `platform.agent_mode=false`, sets `claimed_at`, stamps
+    `user_email`. The api_key value itself never changes.
+    """
+    base_url = (config.platform.base_url or "https://api.mem0.ai").rstrip("/")
+    if not config.platform.api_key or not config.platform.agent_mode:
+        print_error(
+            err_console,
+            "This command requires an active Agent Mode config. Run `mem0 init` first.",
+        )
+        raise typer.Exit(1)
+
+    raw_key = config.platform.api_key
+
+    with httpx.Client(timeout=30.0) as client:
+        # Step 1: request OTP (unless --code provided)
+        if not code:
+            send = client.post(
+                f"{base_url}/api/v1/auth/email_code/",
+                headers={**_SOURCE_HEADERS, "Content-Type": "application/json"},
+                json={"email": email},
+            )
+            if send.status_code == 429:
+                print_error(err_console, "Too many attempts. Try again in a few minutes.")
+                raise typer.Exit(1)
+            if send.status_code != 200:
+                try:
+                    detail = send.json().get("error", send.text)
+                except Exception:
+                    detail = send.text
+                print_error(err_console, f"Failed to send code: {detail}")
+                raise typer.Exit(1)
+
+            print_success(console, f"Verification code sent to {email}. Check your inbox.")
+
+            if not sys.stdin.isatty():
+                print_error(
+                    err_console,
+                    "No --code provided and terminal is non-interactive.",
+                    hint=f"Re-run: mem0 init --email {email} --code <code>",
+                )
+                raise typer.Exit(1)
+
+            console.print()
+            code = Prompt.ask(f"  [{BRAND_COLOR}]Verification Code[/]")
+            if not code:
+                print_error(err_console, "Code is required.")
+                raise typer.Exit(1)
+
+        # Step 2: verify + claim in one shot
+        verify = client.post(
+            f"{base_url}/api/v1/auth/email_code/verify/",
+            headers={**_SOURCE_HEADERS, "Content-Type": "application/json"},
+            json={
+                "email": email,
+                "code": code.strip(),
+                "agent_mode_api_key": raw_key,
+            },
+        )
+
+    if verify.status_code != 200:
+        try:
+            err_body = verify.json()
+            detail = err_body.get("error", verify.text)
+            code_str = err_body.get("code", "")
+        except (json.JSONDecodeError, ValueError, AttributeError):
+            detail = verify.text
+            code_str = ""
+        print_error(err_console, f"Claim failed: {detail}")
+        if code_str == "email_already_claimed":
+            console.print(
+                f"  [{DIM_COLOR}]Tip: this email already has a Mem0 account. Sign in there and run `mem0 link <key>` to attach this agent.[/]"
+            )
+        raise typer.Exit(1)
+
+    claim_body = verify.json()
+    if not claim_body.get("claimed"):
+        print_error(err_console, f"Unexpected verify response: {claim_body}")
+        raise typer.Exit(1)
+
+    config.platform.agent_mode = False
+    config.platform.claimed_at = claim_body.get("claimed_at") or _utcnow_iso()
+    config.platform.user_email = email
+    config.platform.created_via = "email"
+    save_config(config)
+    print_success(console, f"Agent claimed to {email}. Your API key is unchanged.")
+
+
+def _utcnow_iso() -> str:
+    return datetime.now(timezone.utc).isoformat()

cli/python/src/mem0_cli/commands/identify_cmd.py

@@ -0,0 +1,75 @@
+"""mem0 identify — declare which agent owns the current agent-mode key.
+
+Used when `mem0 init --agent` ran without --agent-caller, so the backend
+saved agent_caller=NULL. The agent re-runs `mem0 identify <name>` to PATCH
+its own row with its real identity. Idempotent — running it again just
+overwrites.
+"""
+
+from __future__ import annotations
+
+import httpx
+import typer
+from rich.console import Console
+
+from mem0_cli.branding import print_error, print_success
+from mem0_cli.config import load_config, save_config
+
+console = Console()
+err_console = Console(stderr=True)
+
+_SOURCE_HEADERS = {
+    "X-Mem0-Source": "cli",
+    "X-Mem0-Client-Language": "python",
+}
+
+
+def run_identify(name: str) -> None:
+    """PATCH the active agent-mode key's agent_caller field."""
+    config = load_config()
+    if not config.platform.api_key:
+        print_error(
+            err_console,
+            "No API key configured. Run `mem0 init --agent` first.",
+        )
+        raise typer.Exit(1)
+    if not config.platform.agent_mode:
+        print_error(
+            err_console,
+            "This command only works on unclaimed agent-mode keys.",
+        )
+        raise typer.Exit(1)
+
+    name = (name or "").strip()
+    if not name:
+        print_error(err_console, "Agent name is required.")
+        raise typer.Exit(1)
+
+    base_url = (config.platform.base_url or "https://api.mem0.ai").rstrip("/")
+    try:
+        with httpx.Client(timeout=30.0) as client:
+            resp = client.patch(
+                f"{base_url}/api/v1/auth/agent_mode/caller/",
+                headers={
+                    **_SOURCE_HEADERS,
+                    "Authorization": f"Token {config.platform.api_key}",
+                    "Content-Type": "application/json",
+                },
+                json={"agent_caller": name},
+            )
+    except httpx.HTTPError as exc:
+        print_error(err_console, f"Network error: {exc}")
+        raise typer.Exit(1) from exc
+
+    if resp.status_code != 200:
+        try:
+            detail = resp.json().get("error", resp.text)
+        except Exception:
+            detail = resp.text
+        print_error(err_console, f"Identify failed: {detail}")
+        raise typer.Exit(1)
+
+    canonical = resp.json().get("agent_caller", name)
+    config.platform.agent_caller = canonical
+    save_config(config)
+    print_success(console, f"Identified as {canonical}.")

cli/python/src/mem0_cli/commands/init_cmd.py

@@ -103,6 +103,25 @@ def _validate_email(email: str) -> None:
         raise typer.Exit(1)
 
 
+def _ping_key(api_key: str, base_url: str, timeout: float = 5.0) -> bool:
+    """Validate api_key against /v1/ping/.
+
+    Returns False ONLY on a definitive "invalid key" signal (HTTP 401 / 403).
+    Network errors, timeouts, and 5xx responses return True so we prefer
+    reusing an existing key over silently minting a new shadow on a transient
+    blip (which would also clobber config + plugin-sync targets).
+    """
+    try:
+        resp = httpx.get(
+            f"{base_url.rstrip('/')}/v1/ping/",
+            headers={"Authorization": f"Token {api_key}"},
+            timeout=timeout,
+        )
+    except httpx.HTTPError:
+        return True  # unknown — prefer reuse
+    return resp.status_code not in (401, 403)
+
+
 def _email_login(
     email: str,
     code: str | None,
@@ -182,21 +201,143 @@ def run_init(
     email: str | None = None,
     code: str | None = None,
     force: bool = False,
+    source: str | None = None,
+    agent: bool = False,
+    agent_caller: str | None = None,
 ) -> None:
     """Interactive setup wizard for mem0 CLI.
 
     When both *api_key* and *user_id* are supplied, all prompts are skipped
     (non-interactive mode).  When running in a non-TTY without the required
     flags, an error message is printed.
+
+    Agent Mode dispatch (no email/api-key flags):
+      - If existing config has an active API key → reuse (existing_key path).
+      - Else if any positive agent signal (--agent, --json global, agent env
+        var, or `agent` flag) → POST /api/v1/auth/agent_mode/ and write config.
+      - Else fall through to the interactive wizard.
+
+    Claim dispatch:
+      - If `--email` is set AND existing config has `agent_mode=true`, run the
+        claim device-flow against the existing key instead of minting a new
+        email-based key.
     """
+    from mem0_cli.agent_detect import detect_agent_caller
+    from mem0_cli.commands.agent_mode_cmd import bootstrap_via_backend, claim_via_otp
+    from mem0_cli.state import is_agent_mode as _global_agent_mode
+    from mem0_cli.telemetry import capture_event
+
+    def _fire_init(mode: str, *, claimed: bool = False) -> None:
+        """Fire cli.init telemetry with M1-M6 properties."""
+        props: dict = {"command": "init", "mode": mode}
+        if agent_caller:
+            # Self-declared via --agent-caller; not sniffed from env vars.
+            props["agent_caller"] = agent_caller
+        if source:
+            props["signup_source"] = source
+        if claimed:
+            props["claimed_agent_mode"] = True
+        capture_event("cli.init", props)
+
     config = Mem0Config()
 
     base_url = os.environ.get("MEM0_BASE_URL", config.platform.base_url or DEFAULT_BASE_URL)
+    config.platform.base_url = base_url
 
     if code and not email:
         print_error(err_console, "--code requires --email.")
         raise typer.Exit(1)
 
+    # ── Email + existing agent-mode config → claim flow ─────────────────
+    if email and CONFIG_FILE.exists():
+        existing = load_config()
+        if existing.platform.agent_mode and existing.platform.api_key:
+            email = email.strip().lower()
+            _validate_email(email)
+            print_info(console, f"Claiming Agent Mode account to {email}...")
+            claim_via_otp(existing, email=email, code=code)
+            _fire_init("email", claimed=True)
+            return
+
+    # ── Agent Mode path runs BEFORE the existing-config guard ──────────
+    # Rules 1/2 REUSE a valid existing key (not overwrite), so we must
+    # short-circuit before the guard prompts. Rule 3 mints only when there
+    # is no valid key to reuse — in that case overwriting is correct.
+    _agent_ctx = agent or _global_agent_mode() or (detect_agent_caller() is not None)
+    if not api_key and not email and _agent_ctx:
+        from mem0_cli.output import format_json_envelope
+        from mem0_cli.state import is_agent_mode as _is_json_mode
+
+        def _emit_reuse(source: str) -> None:
+            if _is_json_mode():
+                format_json_envelope(
+                    console,
+                    command="init",
+                    data={
+                        "api_key_saved": False,
+                        "api_key_source": source,
+                        "agent_mode": False,
+                        "message": "Existing Mem0 API key found and reused. No Agent Mode key was created.",
+                    },
+                )
+            else:
+                msg = (
+                    "Existing MEM0_API_KEY is valid; reusing it. No new Agent Mode key was minted."
+                    if source == "env"
+                    else "Existing API key in config is valid; reusing it. No new Agent Mode key was minted."
+                )
+                print_success(console, msg)
+
+        def _maybe_identify(key: str) -> None:
+            """Best-effort PATCH agent_caller when --agent-caller is supplied on a
+            reused key. Silent no-op on any failure — reuse must not break.
+            """
+            if not agent_caller:
+                return
+            try:
+                resp = httpx.patch(
+                    f"{base_url.rstrip('/')}/api/v1/auth/agent_mode/caller/",
+                    headers={
+                        "Authorization": f"Token {key}",
+                        "Content-Type": "application/json",
+                    },
+                    json={"agent_caller": agent_caller},
+                    timeout=10.0,
+                )
+                # Also reflect in local config so introspection matches backend.
+                if resp.status_code == 200 and CONFIG_FILE.exists():
+                    try:
+                        cfg = load_config()
+                        cfg.platform.agent_caller = resp.json().get("agent_caller", agent_caller)
+                        save_config(cfg)
+                    except Exception:
+                        pass
+            except httpx.HTTPError:
+                pass
+
+        # Rule 1: env MEM0_API_KEY valid → reuse, no new key.
+        _env_key = (os.environ.get("MEM0_API_KEY") or "").strip()
+        if _env_key and _ping_key(_env_key, base_url):
+            _maybe_identify(_env_key)
+            _emit_reuse("env")
+            _fire_init("existing_key")
+            return
+        # Rule 2: existing config api_key valid → reuse.
+        if CONFIG_FILE.exists():
+            _existing = load_config()
+            if _existing.platform.api_key and _ping_key(_existing.platform.api_key, base_url):
+                _maybe_identify(_existing.platform.api_key)
+                _emit_reuse("config")
+                _fire_init("existing_key")
+                return
+        # Rule 3: mint a fresh shadow (no valid key to reuse).
+        # agent_caller is the agent's self-declared identity from --agent-caller
+        # (Proof Editor-style). Env-var auto-detect is still used above to
+        # decide we're in an agent context, but never to fill identity.
+        bootstrap_via_backend(config, source=source, agent_caller=agent_caller)
+        _fire_init("agent")
+        return
+
     # Warn if an existing config with an API key would be overwritten
     if not force and CONFIG_FILE.exists():
         existing = load_config()
@@ -242,6 +383,7 @@ def run_init(
         config.platform.api_key = api_key_val
         config.platform.base_url = base_url
         config.platform.user_email = email
+        config.platform.created_via = "email"
         config.defaults.user_id = (
             user_id or os.environ.get("USER") or os.environ.get("USERNAME") or "mem0-cli"
         )
@@ -258,6 +400,8 @@ def run_init(
         return
 
     # ── API key flow (existing) ───────────────────────────────────────
+    # (Agent Mode branch runs earlier — see above, before the existing-config
+    # guard, so Rules 1/2 can REUSE a valid key without prompting overwrite.)
 
     # Non-TTY: resolve defaults so partial flags work in pipelines / CI
     if not sys.stdin.isatty():
@@ -265,7 +409,7 @@ def run_init(
             print_error(
                 err_console,
                 "Non-interactive terminal detected and --api-key is required.",
-                hint="Run: mem0 init --api-key <key> [--user-id <id>]",
+                hint="Run: mem0 init --api-key <key>, --email <addr>, or --agent for unattended Agent Mode bootstrap.",
             )
             raise typer.Exit(1)
         user_id = user_id or os.environ.get("USER") or os.environ.get("USERNAME") or "mem0-cli"
@@ -273,6 +417,7 @@ def run_init(
     # Fully non-interactive when both flags provided
     if api_key and user_id:
         config.platform.api_key = api_key
+        config.platform.created_via = "api_key"
         config.defaults.user_id = user_id
         _validate_platform(config)
         save_config(config)
@@ -313,6 +458,7 @@ def run_init(
             config.platform.api_key = api_key_val
             config.platform.base_url = base_url
             config.platform.user_email = email_addr
+            config.platform.created_via = "email"
             config.defaults.user_id = (
                 user_id or os.environ.get("USER") or os.environ.get("USERNAME") or "mem0-cli"
             )
@@ -331,6 +477,7 @@ def run_init(
     # API key flow
     if api_key:
         config.platform.api_key = api_key
+        config.platform.created_via = "api_key"
     else:
         _setup_platform(config)
 
@@ -370,6 +517,7 @@ def _setup_platform(config: Mem0Config) -> None:
         raise typer.Exit(1)
 
     config.platform.api_key = api_key
+    config.platform.created_via = "api_key"
 
 
 def _setup_defaults(config: Mem0Config) -> None:

cli/python/src/mem0_cli/config.py

@@ -28,6 +28,14 @@ class PlatformConfig:
     api_key: str = ""
     base_url: str = DEFAULT_BASE_URL
     user_email: str = ""
+    # Agent Mode (unclaimed-shadow signup)
+    agent_mode: bool = False  # True while the key is an unclaimed agent-mode key
+    created_via: str = ""  # "agent_mode" | "email" | "api_key" | "existing_key"
+    agent_caller: str = (
+        ""  # canonical agent name when created_via == "agent_mode" (e.g. "claude-code")
+    )
+    claimed_at: str = ""  # ISO timestamp once the agent has been claimed by a human
+    default_user_id: str = ""  # `user_<slug>` returned by bootstrap; used as auto-default
 
 
 @dataclass
@@ -83,6 +91,11 @@ def load_config() -> Mem0Config:
         config.platform.api_key = plat.get("api_key", "")
         config.platform.base_url = plat.get("base_url", DEFAULT_BASE_URL)
         config.platform.user_email = plat.get("user_email", "")
+        config.platform.agent_mode = bool(plat.get("agent_mode", False))
+        config.platform.created_via = plat.get("created_via", "")
+        config.platform.agent_caller = plat.get("agent_caller", "")
+        config.platform.claimed_at = plat.get("claimed_at", "")
+        config.platform.default_user_id = plat.get("default_user_id", "")
 
         defaults = data.get("defaults", {})
         config.defaults.user_id = defaults.get("user_id", "")
@@ -136,6 +149,11 @@ def save_config(config: Mem0Config) -> None:
             "api_key": config.platform.api_key,
             "base_url": config.platform.base_url,
             "user_email": config.platform.user_email,
+            "agent_mode": config.platform.agent_mode,
+            "created_via": config.platform.created_via,
+            "agent_caller": config.platform.agent_caller,
+            "claimed_at": config.platform.claimed_at,
+            "default_user_id": config.platform.default_user_id,
         },
         "telemetry": {
             "anonymous_id": config.telemetry.anonymous_id,
@@ -147,6 +165,19 @@ def save_config(config: Mem0Config) -> None:
 
     os.chmod(CONFIG_FILE, stat.S_IRUSR | stat.S_IWUSR)  # 0600
 
+    # Propagate the active api_key to ecosystem touchpoints (Claude Code
+    # plugin env injection, shell rc exports). Idempotent — only updates
+    # EXISTING entries; never creates new ones. Best-effort: any IOError
+    # in the sync is swallowed so config.json is always the authoritative
+    # write, never blocked by plugin-state issues.
+    if config.platform.api_key:
+        try:
+            from mem0_cli.plugin_sync import sync_api_key
+
+            sync_api_key(config.platform.api_key)
+        except Exception:
+            pass
+
 
 def redact_key(key: str) -> str:
     """Redact an API key for display: m0-xxx...xxx"""

cli/python/src/mem0_cli/output.py

@@ -229,6 +229,16 @@ def format_json_envelope(
     if error:
         envelope["error"] = error
     envelope["data"] = data
+
+    # If the platform flagged this as an unclaimed Agent Mode account, surface
+    # the notice inside the JSON envelope so an agent consuming the output
+    # sees it without needing to inspect HTTP headers.
+    from mem0_cli.state import take_notice
+
+    notice = take_notice()
+    if notice:
+        envelope["mem0_notice"] = notice
+
     console.print_json(json.dumps(envelope, default=str))
 
 
@@ -323,6 +333,15 @@ def format_agent_envelope(
     if count is not None:
         envelope["count"] = count
     envelope["data"] = sanitize_agent_data(command, data)
+
+    # Surface the unclaimed-Agent-Mode notice (if any) in the envelope so an
+    # agent reading the JSON output sees it without inspecting HTTP headers.
+    from mem0_cli.state import take_notice
+
+    notice = take_notice()
+    if notice:
+        envelope["mem0_notice"] = notice
+
     console.print_json(json.dumps(envelope, default=str))
 
 

cli/python/src/mem0_cli/plugin_sync.py

@@ -0,0 +1,119 @@
+"""Sync the active Mem0 API key into other ecosystem touchpoints.
+
+Why this exists:
+  The CLI canonical state lives in ``~/.mem0/config.json``. But MCP servers
+  (Claude Code plugin, Codex plugin, etc.) read ``MEM0_API_KEY`` from env
+  vars or their own config files. Without a sync, an agent-mode bootstrap
+  mints a new key into config.json but the plugin's MCP keeps using the
+  old key from env — silent surprise.
+
+Design:
+  - Update ONLY entries that already exist (never create new ones)
+  - Preserve all surrounding content / formatting / other keys
+  - Atomic writes (tmpfile + rename) so a crash mid-write doesn't corrupt
+  - Idempotent — re-running with the same key is a no-op
+  - Skip on dry_run
+
+Targets currently handled:
+  - ``~/.claude/settings.json::env::MEM0_API_KEY`` (Claude Code env injection)
+  - ``~/.zshrc`` / ``~/.bashrc`` ``export MEM0_API_KEY="..."`` lines
+
+Out of scope (deliberately not touched):
+  - Codex / Cursor MCP configs — would require schema-aware edits and
+    those tools don't have mem0 entries by default
+  - Plugin's own ``<plugin-dir>/.api_key`` file — plugin-managed
+"""
+
+from __future__ import annotations
+
+import contextlib
+import json
+import os
+import re
+import tempfile
+from pathlib import Path
+
+# Files we know how to update safely.
+_CLAUDE_SETTINGS = Path.home() / ".claude" / "settings.json"
+_SHELL_RCS = [Path.home() / ".zshrc", Path.home() / ".bashrc", Path.home() / ".bash_profile"]
+
+
+def sync_api_key(api_key: str) -> list[str]:
+    """Propagate ``api_key`` into known ecosystem touchpoints.
+
+    Returns the list of paths actually updated. Empty list means nothing
+    needed updating (either targets didn't exist or already had this value).
+    """
+    if not api_key:
+        return []
+    updated: list[str] = []
+    if _update_claude_settings(_CLAUDE_SETTINGS, api_key):
+        updated.append(str(_CLAUDE_SETTINGS))
+    for rc in _SHELL_RCS:
+        if _update_shell_rc(rc, api_key):
+            updated.append(str(rc))
+    return updated
+
+
+def _update_claude_settings(path: Path, api_key: str) -> bool:
+    """Update ``env.MEM0_API_KEY`` in path. Returns True if file was changed."""
+    if not path.is_file():
+        return False
+    try:
+        with path.open("r", encoding="utf-8") as f:
+            data = json.load(f)
+    except (json.JSONDecodeError, OSError):
+        return False
+    env = data.get("env")
+    if not isinstance(env, dict) or "MEM0_API_KEY" not in env:
+        # No existing entry — don't create one.
+        return False
+    if env["MEM0_API_KEY"] == api_key:
+        return False  # already in sync
+    env["MEM0_API_KEY"] = api_key
+    _atomic_write_text(path, json.dumps(data, indent=2, ensure_ascii=False) + "\n")
+    return True
+
+
+# Match `export MEM0_API_KEY="..."` (or single quotes, or no quotes).
+# Use [ \t]* (not \s*) for trailing whitespace so a trailing newline at
+# end-of-file is preserved when MEM0_API_KEY is the last line.
+_RC_LINE = re.compile(
+    r'^([ \t]*export[ \t]+MEM0_API_KEY[ \t]*=[ \t]*)(["\']?)([^"\'\n]*)(["\']?)[ \t]*$',
+    re.MULTILINE,
+)
+
+
+def _update_shell_rc(path: Path, api_key: str) -> bool:
+    """Update an existing ``export MEM0_API_KEY=...`` line in path."""
+    if not path.is_file():
+        return False
+    try:
+        text = path.read_text(encoding="utf-8")
+    except OSError:
+        return False
+    match = _RC_LINE.search(text)
+    if not match:
+        return False  # no existing line
+    if match.group(3) == api_key:
+        return False
+    new_text = _RC_LINE.sub(lambda m: f'{m.group(1)}"{api_key}"', text, count=1)
+    _atomic_write_text(path, new_text)
+    return True
+
+
+def _atomic_write_text(path: Path, content: str) -> None:
+    """Write content to path atomically (temp + rename)."""
+    dirname = path.parent
+    fd, tmp_path = tempfile.mkstemp(prefix=f".{path.name}.", suffix=".tmp", dir=dirname)
+    try:
+        with os.fdopen(fd, "w", encoding="utf-8") as f:
+            f.write(content)
+        # Preserve mode if the original existed.
+        if path.exists():
+            os.chmod(tmp_path, path.stat().st_mode & 0o777)
+        os.replace(tmp_path, path)
+    except Exception:
+        with contextlib.suppress(OSError):
+            os.unlink(tmp_path)
+        raise

cli/python/src/mem0_cli/state.py

@@ -4,6 +4,7 @@ from __future__ import annotations
 
 _agent_mode: bool = False
 _current_command: str = ""
+_pending_notice: str = ""
 
 
 def is_agent_mode() -> bool:
@@ -22,3 +23,23 @@ def get_current_command() -> str:
 def set_current_command(name: str) -> None:
     global _current_command
     _current_command = name
+
+
+def capture_notice(notice: str | None) -> None:
+    """Stash a Mem0 backend notice for end-of-command surfacing.
+
+    Called from the platform backend after each response so the notice can
+    be printed once per command (regardless of how many sub-requests fired).
+    Last-write-wins is fine — the message text is identical across requests.
+    """
+    global _pending_notice
+    if notice:
+        _pending_notice = notice
+
+
+def take_notice() -> str:
+    """Return and clear the pending notice."""
+    global _pending_notice
+    msg = _pending_notice
+    _pending_notice = ""
+    return msg

cli/python/src/mem0_cli/telemetry.py

@@ -87,7 +87,6 @@ def capture_event(
     try:
         from mem0_cli import __version__
         from mem0_cli.config import CONFIG_FILE, load_config, save_config
-        from mem0_cli.state import is_agent_mode
 
         config = load_config()
         distinct_id = pre_resolved_email or _get_distinct_id()
@@ -107,6 +106,9 @@ def capture_event(
             with contextlib.suppress(Exception):
                 save_config(config)
 
+        # M4: every cli.* event carries agent_mode based on the config flag
+        # (unclaimed Agent Mode key). This is the growth-doc property used to
+        # join init → add → search funnels in PostHog.
         payload = {
             "api_key": POSTHOG_API_KEY,
             "distinct_id": distinct_id,
@@ -115,7 +117,7 @@ def capture_event(
                 "source": "CLI",
                 "language": "python",
                 "cli_version": __version__,
-                "agent_mode": is_agent_mode(),
+                "agent_mode": bool(config.platform.agent_mode),
                 "python_version": sys.version,
                 "os": sys.platform,
                 "os_version": platform.version(),

cli/python/tests/test_agent_mode.py

@@ -0,0 +1,157 @@
+"""Parity tests for `mem0 init --agent` (Agent Mode bootstrap).
+
+Mirror of ``cli/node/tests/agent-mode.test.ts`` — both files MUST stay in
+sync so that the Python and Node CLIs expose an identical surface for the
+Agent Mode entrypoint. If you add a flag here, add the same assertion on
+the Node side (and vice versa).
+
+Network-bound bootstrap is covered by the platform-side E2E suite
+(``backend/tests/e2e/test_05_agent_mode.py``); these tests only verify
+the CLI surface that ships in the binary.
+"""
+
+from __future__ import annotations
+
+import os
+import re
+import subprocess
+import sys
+
+import pytest
+
+_ANSI_RE = re.compile(r"\x1b\[[0-9;]*[mKJHABCDfsu]")
+
+
+def _strip_ansi(text: str) -> str:
+    return _ANSI_RE.sub("", text)
+
+
+def _run(args: list[str], home_dir: str | None = None) -> subprocess.CompletedProcess:
+    env = os.environ.copy()
+    for key in list(env.keys()):
+        if key.startswith("MEM0_"):
+            del env[key]
+    env.pop("FORCE_COLOR", None)
+    if home_dir:
+        env["HOME"] = home_dir
+    result = subprocess.run(
+        [sys.executable, "-m", "mem0_cli", *args],
+        capture_output=True,
+        text=True,
+        env=env,
+        timeout=15,
+    )
+    return subprocess.CompletedProcess(
+        args=result.args,
+        returncode=result.returncode,
+        stdout=_strip_ansi(result.stdout),
+        stderr=_strip_ansi(result.stderr),
+    )
+
+
+@pytest.fixture
+def clean_home(tmp_path):
+    return str(tmp_path)
+
+
+class TestInitFlagSurface:
+    """`mem0 init --help` must expose the Agent Mode flags."""
+
+    def test_init_help_lists_agent_flag(self):
+        result = _run(["init", "--help"])
+        assert result.returncode == 0
+        assert "--agent" in result.stdout
+
+    def test_init_help_describes_agent_mode(self):
+        result = _run(["init", "--help"])
+        assert result.returncode == 0
+        # Description must mention what --agent actually does so an agent
+        # reading the help can self-discover the bootstrap entrypoint.
+        assert "Agent Mode" in result.stdout or "unattended" in result.stdout.lower()
+
+    def test_init_help_lists_source_flag(self):
+        result = _run(["init", "--help"])
+        assert result.returncode == 0
+        assert "--source" in result.stdout
+
+    def test_init_help_lists_email_and_code(self):
+        # Claim flow flags must remain present alongside Agent Mode flags.
+        result = _run(["init", "--help"])
+        assert result.returncode == 0
+        assert "--email" in result.stdout
+        assert "--code" in result.stdout
+
+
+class TestArgvPreprocessing:
+    """`--agent` on `init` must reach init_cmd, not be eaten by the global preprocessor.
+
+    Regression for the bug where the top-level `--agent` JSON-alias was
+    stripped from ``sys.argv`` before Typer could bind it to the init
+    subcommand, making ``mem0 init --agent`` indistinguishable from a
+    plain ``mem0 init`` (interactive wizard).
+    """
+
+    def test_init_with_agent_reaches_subcommand(self, clean_home):
+        # We can't hit a real backend in unit tests, so we point the CLI at
+        # a guaranteed-dead URL and assert the failure is the bootstrap
+        # request failing — proving the --agent flag was honored and the
+        # bootstrap branch ran, not the interactive wizard.
+        result = subprocess.run(
+            [sys.executable, "-m", "mem0_cli", "init", "--agent"],
+            capture_output=True,
+            text=True,
+            env={
+                **{k: v for k, v in os.environ.items() if not k.startswith("MEM0_")},
+                "HOME": clean_home,
+                "MEM0_BASE_URL": "http://127.0.0.1:1",  # blackhole
+                "FORCE_COLOR": "0",
+            },
+            timeout=15,
+        )
+        combined = _strip_ansi(result.stdout + result.stderr).lower()
+        # Either we got a connection/network error from the bootstrap POST,
+        # or the CLI surfaced an Agent Mode-specific failure message.
+        assert (
+            "agent" in combined
+            or "connect" in combined
+            or "network" in combined
+            or "fetch" in combined
+            or "bootstrap" in combined
+        ), f"Expected bootstrap attempt, got: {combined!r}"
+
+
+class TestJsonEnvelopeParity:
+    """`mem0 init --agent --json` should produce a JSON envelope on success.
+
+    Without a live backend we can only assert the failure shape: when the
+    backend is unreachable, the CLI must still exit non-zero AND not crash
+    on a Python traceback (which would mean we leaked an exception past
+    the agent-mode handler).
+    """
+
+    def test_init_agent_json_no_traceback_on_network_failure(self, clean_home):
+        result = subprocess.run(
+            [sys.executable, "-m", "mem0_cli", "init", "--agent", "--json"],
+            capture_output=True,
+            text=True,
+            env={
+                **{k: v for k, v in os.environ.items() if not k.startswith("MEM0_")},
+                "HOME": clean_home,
+                "MEM0_BASE_URL": "http://127.0.0.1:1",
+                "FORCE_COLOR": "0",
+            },
+            timeout=15,
+        )
+        combined = _strip_ansi(result.stdout + result.stderr)
+        assert "Traceback (most recent call last)" not in combined
+        assert result.returncode != 0
+
+
+class TestInitInCommandList:
+    """`mem0 --help` must list `init` so agents walking the top-level help
+    can discover the Agent Mode entrypoint without prior knowledge."""
+
+    def test_top_level_help_lists_init(self):
+        result = _run(["--help"])
+        assert result.returncode == 0
+        assert "init" in result.stdout

cli/python/tests/test_init_internals.py

@@ -0,0 +1,206 @@
+"""Unit tests for init internals — decision tree primitives + plugin sync.
+
+These tests exercise the units that the high-level subprocess parity tests in
+``test_agent_mode.py`` deliberately can't reach:
+
+  - ``_ping_key`` must NOT treat network errors as "invalid key" (else a VPN
+    flap silently mints a new shadow over a working key).
+  - ``plugin_sync`` must only update entries that already exist, preserve
+    trailing newlines, and never mangle other lines.
+  - The 403→ratelimit translation in ``bootstrap_via_backend`` surfaces the
+    real cause instead of DRF's opaque "You do not have permission" string.
+
+Mirror surface lives in ``cli/node/tests/agent-mode.test.ts``; if you add a
+behavioral assertion here, mirror it on the Node side and vice versa.
+"""
+
+from __future__ import annotations
+
+from unittest.mock import MagicMock
+
+import httpx
+import pytest
+
+from mem0_cli.commands.init_cmd import _ping_key
+from mem0_cli.plugin_sync import _update_claude_settings, _update_shell_rc
+
+# ── _ping_key ──────────────────────────────────────────────────────────────
+
+
+class _Resp:
+    def __init__(self, status_code: int) -> None:
+        self.status_code = status_code
+
+
+def test_ping_key_200_is_valid(monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.setattr(httpx, "get", lambda *a, **kw: _Resp(200))
+    assert _ping_key("k", "http://x") is True
+
+
+def test_ping_key_401_is_invalid(monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.setattr(httpx, "get", lambda *a, **kw: _Resp(401))
+    assert _ping_key("k", "http://x") is False
+
+
+def test_ping_key_403_is_invalid(monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.setattr(httpx, "get", lambda *a, **kw: _Resp(403))
+    assert _ping_key("k", "http://x") is False
+
+
+def test_ping_key_5xx_is_not_definitively_invalid(monkeypatch: pytest.MonkeyPatch) -> None:
+    # Transient upstream failure must NOT cause a shadow to be minted.
+    monkeypatch.setattr(httpx, "get", lambda *a, **kw: _Resp(503))
+    assert _ping_key("k", "http://x") is True
+
+
+def test_ping_key_connect_error_prefers_reuse(monkeypatch: pytest.MonkeyPatch) -> None:
+    # Network blip (DNS, captive portal, etc.) — must NOT trigger a re-mint.
+    def boom(*a, **kw):
+        raise httpx.ConnectError("nope")
+
+    monkeypatch.setattr(httpx, "get", boom)
+    assert _ping_key("k", "http://x") is True
+
+
+def test_ping_key_timeout_prefers_reuse(monkeypatch: pytest.MonkeyPatch) -> None:
+    def boom(*a, **kw):
+        raise httpx.ReadTimeout("slow")
+
+    monkeypatch.setattr(httpx, "get", boom)
+    assert _ping_key("k", "http://x") is True
+
+
+# ── plugin_sync._update_shell_rc ──────────────────────────────────────────
+
+
+def test_shell_rc_updates_existing_export_preserves_trailing_newline(tmp_path) -> None:
+    rc = tmp_path / ".zshrc"
+    rc.write_text('export MEM0_API_KEY="old"\n', encoding="utf-8")
+    changed = _update_shell_rc(rc, "newkey")
+    assert changed is True
+    assert rc.read_text(encoding="utf-8") == 'export MEM0_API_KEY="newkey"\n'
+
+
+def test_shell_rc_does_not_create_new_export(tmp_path) -> None:
+    rc = tmp_path / ".zshrc"
+    rc.write_text("alias ll='ls -la'\n", encoding="utf-8")
+    changed = _update_shell_rc(rc, "newkey")
+    assert changed is False
+    assert rc.read_text(encoding="utf-8") == "alias ll='ls -la'\n"
+
+
+def test_shell_rc_preserves_surrounding_content(tmp_path) -> None:
+    rc = tmp_path / ".zshrc"
+    original = "# my zshrc\nalias ll='ls -la'\nexport MEM0_API_KEY='old'\nexport OTHER=keepme\n"
+    rc.write_text(original, encoding="utf-8")
+    _update_shell_rc(rc, "newkey")
+    after = rc.read_text(encoding="utf-8")
+    assert "alias ll='ls -la'\n" in after
+    assert "export OTHER=keepme\n" in after
+    assert "# my zshrc\n" in after
+    assert 'export MEM0_API_KEY="newkey"\n' in after
+
+
+def test_shell_rc_idempotent_when_already_matching(tmp_path) -> None:
+    rc = tmp_path / ".zshrc"
+    rc.write_text('export MEM0_API_KEY="same"\n', encoding="utf-8")
+    assert _update_shell_rc(rc, "same") is False
+
+
+def test_shell_rc_missing_file_is_noop(tmp_path) -> None:
+    rc = tmp_path / ".zshrc"  # does not exist
+    assert _update_shell_rc(rc, "x") is False
+
+
+# ── plugin_sync._update_claude_settings ────────────────────────────────────
+
+
+def test_claude_settings_does_not_create_env_block(tmp_path) -> None:
+    import json
+
+    settings = tmp_path / "settings.json"
+    settings.write_text(json.dumps({"otherKey": 1}), encoding="utf-8")
+    changed = _update_claude_settings(settings, "newkey")
+    assert changed is False
+    # Original content unchanged.
+    assert json.loads(settings.read_text(encoding="utf-8")) == {"otherKey": 1}
+
+
+def test_claude_settings_does_not_create_mem0_entry_in_existing_env(tmp_path) -> None:
+    import json
+
+    settings = tmp_path / "settings.json"
+    settings.write_text(json.dumps({"env": {"OTHER_KEY": "x"}}), encoding="utf-8")
+    changed = _update_claude_settings(settings, "newkey")
+    assert changed is False
+
+
+def test_claude_settings_updates_existing_entry(tmp_path) -> None:
+    import json
+
+    settings = tmp_path / "settings.json"
+    settings.write_text(
+        json.dumps({"env": {"MEM0_API_KEY": "old", "OTHER": "y"}}, indent=2),
+        encoding="utf-8",
+    )
+    changed = _update_claude_settings(settings, "fresh")
+    assert changed is True
+    data = json.loads(settings.read_text(encoding="utf-8"))
+    assert data["env"]["MEM0_API_KEY"] == "fresh"
+    assert data["env"]["OTHER"] == "y"  # other keys preserved
+
+
+def test_claude_settings_idempotent(tmp_path) -> None:
+    import json
+
+    settings = tmp_path / "settings.json"
+    settings.write_text(json.dumps({"env": {"MEM0_API_KEY": "same"}}), encoding="utf-8")
+    assert _update_claude_settings(settings, "same") is False
+
+
+def test_claude_settings_malformed_json_is_noop(tmp_path) -> None:
+    settings = tmp_path / "settings.json"
+    settings.write_text("{ this is not json", encoding="utf-8")
+    assert _update_claude_settings(settings, "x") is False
+
+
+# ── bootstrap rate-limit translation ──────────────────────────────────────
+
+
+def test_bootstrap_403_permission_surfaces_ratelimit(monkeypatch, capsys) -> None:
+    """DRF 403 'You do not have permission' must be translated to the daily limit message."""
+    from mem0_cli.commands.agent_mode_cmd import bootstrap_via_backend
+    from mem0_cli.config import Mem0Config
+
+    fake_resp = MagicMock()
+    fake_resp.status_code = 403
+    fake_resp.text = '{"detail": "You do not have permission to perform this action."}'
+    fake_resp.json = MagicMock(
+        return_value={"detail": "You do not have permission to perform this action."}
+    )
+
+    class _Client:
+        def __init__(self, *a, **kw):
+            pass
+
+        def __enter__(self):
+            return self
+
+        def __exit__(self, *a):
+            return False
+
+        def post(self, *a, **kw):
+            return fake_resp
+
+    monkeypatch.setattr(httpx, "Client", _Client)
+    cfg = Mem0Config()
+    cfg.platform.base_url = "https://api.mem0.ai"
+    import typer
+
+    with pytest.raises(typer.Exit):
+        bootstrap_via_backend(cfg)
+
+    captured = capsys.readouterr()
+    combined = captured.out + captured.err
+    assert "Daily Agent Mode signup limit reached" in combined
+    assert "permission to perform this action" not in combined