diff --git a/cli/pkg/client.go b/cli/pkg/client.go
index 8d41c148e..78f06b050 100644
--- a/cli/pkg/client.go
+++ b/cli/pkg/client.go
@@ -70,6 +70,12 @@ type APIError struct {
 	Body       string
 	Message    string
 	Data       interface{}
+	// Hint is an optional human-readable suggestion appended to the error
+	// message. Used to surface common-misconfiguration tips that the server
+	// response itself cannot convey (for example, an API path-segment
+	// mismatch between the CLI's configured api.name and the deployed
+	// server's actual path).
+	Hint string
 }
 
 func (e *APIError) Error() string {
@@ -77,13 +83,17 @@ func (e *APIError) Error() string {
 	if msg == "" {
 		msg = e.Body
 	}
+	base := fmt.Sprintf("API error %d: %s", e.StatusCode, msg)
 	if e.Data != nil {
 		dataJSON, err := json.Marshal(e.Data)
 		if err == nil && string(dataJSON) != "null" {
-			return fmt.Sprintf("API error %d: %s\nDetails: %s", e.StatusCode, msg, string(dataJSON))
+			base = fmt.Sprintf("%s\nDetails: %s", base, string(dataJSON))
 		}
 	}
-	return fmt.Sprintf("API error %d: %s", e.StatusCode, msg)
+	if e.Hint != "" {
+		return base + "\nHint: " + e.Hint
+	}
+	return base
 }
 
 func NewClient(baseURL, org, token string, log *logrus.Entry, debug bool) *Client {
@@ -266,12 +276,48 @@ func (c *Client) do(method, pathTemplate string, pathParams, queryParams map[str
 			}
 			apiErr.Data = errResp.Data
 		}
+		if hint := apiNameMismatchHint(resp.StatusCode, path); hint != "" {
+			apiErr.Hint = hint
+		}
 		return nil, nil, apiErr
 	}
 
 	return respBody, resp.Header, nil
 }
 
+// apiNameMismatchHint returns a suggestion for users hitting 404 on an
+// org-scoped API path whose API-name segment likely does not match what the
+// server actually serves. Older (pre-rename) deployments respond on
+// `/v2/org/{org}/carbide/...`; current deployments respond on
+// `/v2/org/{org}/nico/...`. When a 404 lands on either of those segments,
+// the most common cause is an api.name config mismatch, not a missing
+// resource. Returns "" for unrelated 4xx, non-404 statuses, or paths that do
+// not look API-name-segmented.
+func apiNameMismatchHint(statusCode int, path string) string {
+	if statusCode != http.StatusNotFound {
+		return ""
+	}
+	m := orgScopedAPIPathPattern.FindStringSubmatch(path)
+	if len(m) < 3 {
+		return ""
+	}
+	segment := m[2]
+	var alternate string
+	switch segment {
+	case "nico":
+		alternate = "carbide"
+	case "carbide":
+		alternate = "nico"
+	default:
+		return ""
+	}
+	return fmt.Sprintf(
+		"the server returned 404 for path segment %q. Older deployments serve on %q. "+
+			"If this resource exists, set api.name to %q in your config (~/.nico/config.yaml).",
+		segment, alternate, alternate,
+	)
+}
+
 func formatDebugBody(body []byte) string {
 	if len(body) == 0 {
 		return "<empty>"
diff --git a/cli/pkg/client_test.go b/cli/pkg/client_test.go
index f72f335b3..cc2f0adbd 100644
--- a/cli/pkg/client_test.go
+++ b/cli/pkg/client_test.go
@@ -201,3 +201,88 @@ func TestClientDoDoesNotRefreshOnForbidden(t *testing.T) {
 	require.Equal(t, http.StatusForbidden, apiErr.StatusCode)
 	require.Equal(t, 0, refreshes)
 }
+
+func TestAPINameMismatchHint(t *testing.T) {
+	cases := []struct {
+		name       string
+		statusCode int
+		path       string
+		wantHas    string
+		wantEmpty  bool
+	}{
+		{
+			name:       "404 on nico segment suggests carbide",
+			statusCode: http.StatusNotFound,
+			path:       "/v2/org/ncx/nico/site",
+			wantHas:    `set api.name to "carbide"`,
+		},
+		{
+			name:       "404 on carbide segment suggests nico",
+			statusCode: http.StatusNotFound,
+			path:       "/v2/org/ncx/carbide/site",
+			wantHas:    `set api.name to "nico"`,
+		},
+		{
+			name:       "non-404 status returns empty hint",
+			statusCode: http.StatusInternalServerError,
+			path:       "/v2/org/ncx/nico/site",
+			wantEmpty:  true,
+		},
+		{
+			name:       "404 on non-API-name path returns empty hint",
+			statusCode: http.StatusNotFound,
+			path:       "/healthz",
+			wantEmpty:  true,
+		},
+		{
+			name:       "404 on unrelated org-scoped segment returns empty hint",
+			statusCode: http.StatusNotFound,
+			path:       "/v2/org/ncx/something-else/site",
+			wantEmpty:  true,
+		},
+	}
+	for _, tc := range cases {
+		t.Run(tc.name, func(t *testing.T) {
+			got := apiNameMismatchHint(tc.statusCode, tc.path)
+			if tc.wantEmpty {
+				require.Empty(t, got)
+				return
+			}
+			require.Contains(t, got, tc.wantHas)
+		})
+	}
+}
+
+func TestClientDoAddsAPINameHintOn404(t *testing.T) {
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, _ *http.Request) {
+		http.Error(w, `{"message":"not found"}`, http.StatusNotFound)
+	}))
+	defer server.Close()
+
+	client := NewClient(server.URL, "test-org", "token", nil, false)
+	_, _, err := client.Do("GET", "/v2/org/{org}/nico/site", nil, nil, nil)
+	apiErr, ok := err.(*APIError)
+	require.True(t, ok, "err = %T, want *APIError", err)
+	require.Equal(t, http.StatusNotFound, apiErr.StatusCode)
+	require.Contains(t, apiErr.Hint, `set api.name to "carbide"`)
+	require.Contains(t, apiErr.Error(), "Hint:")
+}
+
+func TestAPIErrorErrorIncludesHintAndDetails(t *testing.T) {
+	e := &APIError{
+		StatusCode: 404,
+		Message:    "not found",
+		Data:       map[string]string{"path": "/x"},
+		Hint:       "try foo",
+	}
+	got := e.Error()
+	require.Contains(t, got, "API error 404")
+	require.Contains(t, got, "Details:")
+	require.Contains(t, got, "Hint: try foo")
+}
+
+func TestAPIErrorErrorOmitsHintWhenEmpty(t *testing.T) {
+	e := &APIError{StatusCode: 500, Message: "boom"}
+	got := e.Error()
+	require.NotContains(t, got, "Hint:")
+}