diff --git a/api/app/settings/common.py b/api/app/settings/common.py
index 0ebbc0ec3cc1..7cfdb5ee3738 100644
--- a/api/app/settings/common.py
+++ b/api/app/settings/common.py
@@ -397,6 +397,7 @@
     "django.contrib.messages.middleware.MessageMiddleware",
     "django.middleware.clickjacking.XFrameOptionsMiddleware",
     "simple_history.middleware.HistoryRequestMiddleware",
+    "telemetry.middleware.CLIUsageLoggerMiddleware",
     "telemetry.middleware.MCPUsageLoggerMiddleware",  # Must come last!
 ]
 
diff --git a/api/projects/views.py b/api/projects/views.py
index 8274dd79cd5f..8aa59f5fc6e5 100644
--- a/api/projects/views.py
+++ b/api/projects/views.py
@@ -48,6 +48,7 @@
     ProjectRetrieveSerializer,
     ProjectUpdateSerializer,
 )
+from telemetry.spans import set_span_attribute
 from users.models import FFAdminUser
 
 
@@ -81,6 +82,17 @@ def get_serializer_class(self):  # type: ignore[no-untyped-def]
 
     pagination_class = None
 
+    def list(self, request, *args, **kwargs):  # type: ignore[no-untyped-def]
+        response = super().list(request, *args, **kwargs)
+
+        if response.data and (
+            organisation_id := request.query_params.get("organisation")
+        ):
+            # get_queryset validates the ID and restricts results to permitted projects.
+            set_span_attribute("organisation.id", int(organisation_id))
+
+        return response
+
     def get_serializer_context(self):  # type: ignore[no-untyped-def]
         return super().get_serializer_context()
 
diff --git a/api/telemetry/middleware.py b/api/telemetry/middleware.py
index 7754a686f523..358ab26be956 100644
--- a/api/telemetry/middleware.py
+++ b/api/telemetry/middleware.py
@@ -1,4 +1,6 @@
+import re
 from collections.abc import Callable
+from typing import cast
 
 import structlog
 from django.http.request import HttpRequest
@@ -7,6 +9,29 @@
 
 from telemetry.spans import get_span_attribute
 
+CLI_USER_AGENT_PATTERN = re.compile(
+    r"^flagsmith-cli/(?P<version>.+) \((?P<os>[^/()]+)/(?P<arch>[^/()]+)\)$"
+)
+
+
+def _get_organisation_id_from_request_context(
+    request: HttpRequest,
+) -> int | None:
+    # Set by the permission layer for organisations the user belongs to
+    if isinstance(
+        organisation_id := get_span_attribute("organisation.id"),
+        int,
+    ):
+        return organisation_id
+
+    if getattr(request.user, "is_master_api_key_user", False):
+        from api_keys.user import APIKeyUser
+
+        assert isinstance(request.user, APIKeyUser)
+        return cast(int, request.user.key.organisation_id)
+
+    return None
+
 
 class MCPUsageLoggerMiddleware:
     """Emit telemetry events for MCP usage"""
@@ -45,8 +70,9 @@ def _get_organisation_id(self, request: HttpRequest) -> int | None:
         """Obtain the organisation ID from the request context."""
         from organisations.models import Organisation
 
-        # Set by the permission layer for organisations the user belongs to
-        if isinstance(organisation_id := get_span_attribute("organisation.id"), int):
+        if (
+            organisation_id := _get_organisation_id_from_request_context(request)
+        ) is not None:
             return organisation_id
 
         assert request.user.is_authenticated  # NOTE: protected upstream
@@ -57,3 +83,45 @@ def _get_organisation_id(self, request: HttpRequest) -> int | None:
             Organisation.MultipleObjectsReturned,  # Don't guess
         ):
             return None
+
+
+class CLIUsageLoggerMiddleware:
+    """Emit telemetry events for Flagsmith CLI usage."""
+
+    def __init__(
+        self,
+        get_response: Callable[[HttpRequest], HttpResponse],
+    ) -> None:
+        self.get_response = get_response
+
+    def __call__(self, request: HttpRequest) -> HttpResponse:
+        response = self.get_response(request)
+
+        match = CLI_USER_AGENT_PATTERN.fullmatch(request.headers.get("User-Agent", ""))
+        if match is None:
+            return response
+
+        if not request.user or not request.user.is_authenticated:
+            return response
+
+        event = {
+            "cli__version": match.group("version"),
+            "cli__os": match.group("os"),
+            "cli__arch": match.group("arch"),
+            "status": "error" if response.status_code >= 400 else "success",
+        }
+
+        if (
+            organisation_id := _get_organisation_id_from_request_context(request)
+        ) is not None:
+            event["organisation__id"] = organisation_id
+
+        if not getattr(request.user, "is_master_api_key_user", False):
+            from users.models import FFAdminUser
+
+            assert isinstance(request.user, FFAdminUser)
+            event["amplitude__user_id"] = str(request.user.uuid)
+
+        structlog.get_logger("cli").info("request.made", **event)
+
+        return response
diff --git a/api/tests/unit/telemetry/test_unit_telemetry_middleware.py b/api/tests/unit/telemetry/test_unit_telemetry_middleware.py
index 2ce11324edc0..529aa044aed5 100644
--- a/api/tests/unit/telemetry/test_unit_telemetry_middleware.py
+++ b/api/tests/unit/telemetry/test_unit_telemetry_middleware.py
@@ -1,9 +1,15 @@
 import pytest
+from django.http import HttpRequest, HttpResponse
+from pytest_django import DjangoAssertNumQueries
 from pytest_structlog import StructuredLogCapture
 from rest_framework.test import APIClient
 
+from api_keys.user import APIKeyUser
 from environments.models import Environment
 from organisations.models import Organisation, OrganisationRole
+from projects.models import Project
+from telemetry.middleware import CLIUsageLoggerMiddleware
+from telemetry.spans import set_span_attribute
 from users.models import FFAdminUser
 
 
@@ -166,3 +172,275 @@ def test_mcp_usage_logger_middleware__sdk_request__logs_nothing(
     # Then
     assert response.status_code == 200
     assert log.events == []
+
+
+@pytest.mark.usefixtures("recording_span")
+def test_cli_usage_logger_middleware__authenticated_cli_request__logs_usage_event(
+    staff_client: APIClient,
+    staff_user: FFAdminUser,
+    organisation: Organisation,
+    log: StructuredLogCapture,
+) -> None:
+    # Given
+    set_span_attribute("organisation.id", organisation.pk)
+
+    # When
+    response = staff_client.get(
+        "/api/v1/projects/",
+        HTTP_USER_AGENT="flagsmith-cli/2.0.0-beta.3 (darwin/arm64)",
+    )
+
+    # Then
+    assert response.status_code == 200
+    assert log.events == [
+        {
+            "level": "info",
+            "event": "request.made",
+            "cli__version": "2.0.0-beta.3",
+            "cli__os": "darwin",
+            "cli__arch": "arm64",
+            "organisation__id": organisation.pk,
+            "status": "success",
+            "amplitude__user_id": str(staff_user.uuid),
+        }
+    ]
+
+
+@pytest.mark.usefixtures("recording_span")
+def test_cli_usage_logger_middleware__project_list_with_organisation__logs_organisation_id(
+    admin_client: APIClient,
+    admin_user: FFAdminUser,
+    organisation: Organisation,
+    project: Project,
+    log: StructuredLogCapture,
+) -> None:
+    # Given / When
+    response = admin_client.get(
+        f"/api/v1/projects/?organisation={organisation.pk}",
+        HTTP_USER_AGENT="flagsmith-cli/2.0.0 (linux/amd64)",
+    )
+
+    # Then
+    assert response.status_code == 200
+
+    response_data = response.json()
+    assert any(item["id"] == project.id for item in response_data)
+
+    assert log.events == [
+        {
+            "level": "info",
+            "event": "request.made",
+            "cli__version": "2.0.0",
+            "cli__os": "linux",
+            "cli__arch": "amd64",
+            "organisation__id": organisation.pk,
+            "status": "success",
+            "amplitude__user_id": str(admin_user.uuid),
+        }
+    ]
+
+
+@pytest.mark.usefixtures("recording_span")
+def test_cli_usage_logger_middleware__project_list_with_unpermitted_organisation__does_not_log_organisation_id(
+    staff_client: APIClient,
+    staff_user: FFAdminUser,
+    log: StructuredLogCapture,
+) -> None:
+    # Given
+    other_organisation = Organisation.objects.create(name="Other Org")
+
+    # When
+    response = staff_client.get(
+        f"/api/v1/projects/?organisation={other_organisation.pk}",
+        HTTP_USER_AGENT="flagsmith-cli/2.0.0 (linux/amd64)",
+    )
+
+    # Then
+    assert response.status_code == 200
+    assert log.events == [
+        {
+            "level": "info",
+            "event": "request.made",
+            "cli__version": "2.0.0",
+            "cli__os": "linux",
+            "cli__arch": "amd64",
+            "status": "success",
+            "amplitude__user_id": str(staff_user.uuid),
+        }
+    ]
+
+
+@pytest.mark.usefixtures("recording_span")
+def test_cli_usage_logger_middleware__project_list_with_empty_result__does_not_log_organisation_id(
+    admin_client: APIClient,
+    admin_user: FFAdminUser,
+    organisation: Organisation,
+    log: StructuredLogCapture,
+) -> None:
+    # Given / When
+    response = admin_client.get(
+        f"/api/v1/projects/?organisation={organisation.pk}",
+        HTTP_USER_AGENT="flagsmith-cli/2.0.0 (linux/amd64)",
+    )
+
+    # Then
+    assert response.status_code == 200
+    assert response.json() == []
+
+    assert log.events == [
+        {
+            "level": "info",
+            "event": "request.made",
+            "cli__version": "2.0.0",
+            "cli__os": "linux",
+            "cli__arch": "amd64",
+            "status": "success",
+            "amplitude__user_id": str(admin_user.uuid),
+        }
+    ]
+
+
+def test_cli_usage_logger_middleware__unauthenticated_cli_request__logs_nothing(
+    api_client: APIClient,
+    log: StructuredLogCapture,
+) -> None:
+    # Given / When
+    response = api_client.get(
+        "/api/v1/projects/",
+        HTTP_USER_AGENT="flagsmith-cli/2.0.0 (linux/amd64)",
+    )
+
+    # Then
+    assert response.status_code == 401
+    assert log.events == []
+
+
+def test_cli_usage_logger_middleware__master_api_key_request__logs_organisation_without_amplitude_user_id(
+    admin_master_api_key_client: APIClient,
+    organisation: Organisation,
+    log: StructuredLogCapture,
+) -> None:
+    # Given / When
+    response = admin_master_api_key_client.get(
+        "/api/v1/projects/",
+        HTTP_USER_AGENT="flagsmith-cli/2.0.0 (linux/amd64)",
+    )
+
+    # Then
+    assert response.status_code == 200
+    assert log.events == [
+        {
+            "level": "info",
+            "event": "request.made",
+            "cli__version": "2.0.0",
+            "cli__os": "linux",
+            "cli__arch": "amd64",
+            "organisation__id": organisation.pk,
+            "status": "success",
+        }
+    ]
+
+
+@pytest.mark.usefixtures("recording_span")
+def test_cli_usage_logger_middleware__500_response__logs_error_status(
+    staff_user: FFAdminUser,
+    organisation: Organisation,
+    log: StructuredLogCapture,
+) -> None:
+    # Given
+    set_span_attribute("organisation.id", organisation.pk)
+
+    request = HttpRequest()
+    request.user = staff_user
+    request.META["HTTP_USER_AGENT"] = "flagsmith-cli/2.0.0 (linux/amd64)"
+
+    middleware = CLIUsageLoggerMiddleware(lambda request: HttpResponse(status=500))
+
+    # When
+    response = middleware(request)
+
+    # Then
+    assert response.status_code == 500
+    assert log.events == [
+        {
+            "level": "info",
+            "event": "request.made",
+            "cli__version": "2.0.0",
+            "cli__os": "linux",
+            "cli__arch": "amd64",
+            "organisation__id": organisation.pk,
+            "status": "error",
+            "amplitude__user_id": str(staff_user.uuid),
+        }
+    ]
+
+
+@pytest.mark.usefixtures("recording_span")
+def test_cli_usage_logger_middleware__version_with_spaces__preserves_version_unchanged(
+    staff_user: FFAdminUser,
+    organisation: Organisation,
+    log: StructuredLogCapture,
+) -> None:
+    # Given
+    set_span_attribute("organisation.id", organisation.pk)
+
+    request = HttpRequest()
+    request.user = staff_user
+    request.META["HTTP_USER_AGENT"] = "flagsmith-cli/dev (abcdefg) (linux/amd64)"
+
+    middleware = CLIUsageLoggerMiddleware(lambda request: HttpResponse(status=200))
+
+    # When
+    response = middleware(request)
+
+    # Then
+    assert response.status_code == 200
+    assert log.events == [
+        {
+            "level": "info",
+            "event": "request.made",
+            "cli__version": "dev (abcdefg)",
+            "cli__os": "linux",
+            "cli__arch": "amd64",
+            "organisation__id": organisation.pk,
+            "status": "success",
+            "amplitude__user_id": str(staff_user.uuid),
+        }
+    ]
+
+
+def test_cli_usage_logger_middleware__non_cli_user_agent__logs_nothing(
+    staff_user: FFAdminUser,
+    log: StructuredLogCapture,
+) -> None:
+    # Given
+    request = HttpRequest()
+    request.user = staff_user
+    request.META["HTTP_USER_AGENT"] = "Mozilla/5.0"
+
+    middleware = CLIUsageLoggerMiddleware(lambda request: HttpResponse(status=200))
+
+    # When
+    response = middleware(request)
+
+    # Then
+    assert response.status_code == 200
+    assert log.events == []
+
+
+def test_cli_usage_logger_middleware__master_api_key__makes_no_database_queries(
+    api_key_user: APIKeyUser,
+    django_assert_num_queries: DjangoAssertNumQueries,
+) -> None:
+    # Given
+    request = HttpRequest()
+    setattr(request, "user", api_key_user)
+    request.META["HTTP_USER_AGENT"] = "flagsmith-cli/2.0.0 (linux/amd64)"
+
+    middleware = CLIUsageLoggerMiddleware(lambda request: HttpResponse(status=200))
+
+    # When / Then
+    with django_assert_num_queries(0):
+        response = middleware(request)
+
+    assert response.status_code == 200
diff --git a/docs/docs/deployment-self-hosting/observability/_events-catalogue.md b/docs/docs/deployment-self-hosting/observability/_events-catalogue.md
index 3826b5823873..5b0b2be47d7a 100644
--- a/docs/docs/deployment-self-hosting/observability/_events-catalogue.md
+++ b/docs/docs/deployment-self-hosting/observability/_events-catalogue.md
@@ -563,8 +563,8 @@ Attributes:
 ### `mcp.tool.called`
 
 Logged at `info` from:
- - `api/telemetry/middleware.py:38`
- - `api/telemetry/middleware.py:40`
+ - `api/telemetry/middleware.py:63`
+ - `api/telemetry/middleware.py:65`
 
 Attributes:
  - `organisation.id`