diff --git a/pkg/connector/apikey.go b/pkg/connector/apikey.go
index 3e4784259..b20ee45bd 100644
--- a/pkg/connector/apikey.go
+++ b/pkg/connector/apikey.go
@@ -34,6 +34,13 @@ type APIKeyConnection struct {
 	// It is populated from the provider Registration at connector
 	// creation time.
 	Header string `json:"header,omitempty"`
+	// BasicAuth, when true, presents the API key as the username of an
+	// HTTP Basic credential with an empty password (`Authorization:
+	// Basic base64(<key>:)`) — required by providers such as Cursor
+	// whose Admin API documents Basic auth and rejects Bearer tokens.
+	// It is mutually exclusive with Header and is populated from the
+	// provider Registration at connector creation time.
+	BasicAuth bool `json:"basic_auth,omitempty"`
 }
 
 var _ Connection = (*APIKeyConnection)(nil)
@@ -49,6 +56,15 @@ func (c *APIKeyConnection) Scopes() []string {
 func (c *APIKeyConnection) Client(ctx context.Context) (*http.Client, error) {
 	underlying := httpclient.DefaultPooledTransport(httpclient.WithSSRFProtection())
 
+	if c.BasicAuth {
+		return &http.Client{
+			Transport: &basicAuthTransport{
+				username:   c.APIKey,
+				underlying: underlying,
+			},
+		}, nil
+	}
+
 	if c.Header != "" {
 		return &http.Client{
 			Transport: &apiKeyHeaderTransport{
@@ -86,6 +102,22 @@ func (t *apiKeyHeaderTransport) RoundTrip(req *http.Request) (*http.Response, er
 	return t.underlying.RoundTrip(req2)
 }
 
+// basicAuthTransport presents the API key as the username of an HTTP
+// Basic credential with an empty password. Providers such as Cursor
+// document `-u <key>:` Basic auth for their Admin API and reject Bearer
+// tokens, so neither oauth2Transport nor apiKeyHeaderTransport fits.
+type basicAuthTransport struct {
+	username   string
+	underlying http.RoundTripper
+}
+
+func (t *basicAuthTransport) RoundTrip(req *http.Request) (*http.Response, error) {
+	req2 := req.Clone(req.Context())
+	req2.SetBasicAuth(t.username, "")
+
+	return t.underlying.RoundTrip(req2)
+}
+
 func (c APIKeyConnection) MarshalJSON() ([]byte, error) {
 	type Alias APIKeyConnection
 
diff --git a/pkg/connector/apikey_test.go b/pkg/connector/apikey_test.go
new file mode 100644
index 000000000..b2968cb36
--- /dev/null
+++ b/pkg/connector/apikey_test.go
@@ -0,0 +1,104 @@
+// Copyright (c) 2026 Probo Inc <hello@getprobo.com>.
+//
+// Permission to use, copy, modify, and/or distribute this software for any
+// purpose with or without fee is hereby granted, provided that the above
+// copyright notice and this permission notice appear in all copies.
+//
+// THE SOFTWARE IS PROVIDED "AS IS" AND THE AUTHOR DISCLAIMS ALL WARRANTIES WITH
+// REGARD TO THIS SOFTWARE INCLUDING ALL IMPLIED WARRANTIES OF MERCHANTABILITY
+// AND FITNESS. IN NO EVENT SHALL THE AUTHOR BE LIABLE FOR ANY SPECIAL, DIRECT,
+// INDIRECT, OR CONSEQUENTIAL DAMAGES OR ANY DAMAGES WHATSOEVER RESULTING FROM
+// LOSS OF USE, DATA OR PROFITS, WHETHER IN AN ACTION OF CONTRACT, NEGLIGENCE OR
+// OTHER TORTIOUS ACTION, ARISING OUT OF OR IN CONNECTION WITH THE USE OR
+// PERFORMANCE OF THIS SOFTWARE.
+
+package connector
+
+import (
+	"context"
+	"net/http"
+	"net/http/httptest"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+)
+
+// recordingRoundTripper captures the last request it sees and returns a
+// canned 200 response without touching the network, so transport
+// behaviour can be asserted without tripping SSRF protection.
+type recordingRoundTripper struct {
+	lastRequest *http.Request
+}
+
+func (rt *recordingRoundTripper) RoundTrip(req *http.Request) (*http.Response, error) {
+	rt.lastRequest = req
+
+	return &http.Response{
+		StatusCode: http.StatusOK,
+		Body:       http.NoBody,
+		Header:     make(http.Header),
+		Request:    req,
+	}, nil
+}
+
+func TestBasicAuthTransport_RoundTrip(t *testing.T) {
+	t.Parallel()
+
+	rec := &recordingRoundTripper{}
+	transport := &basicAuthTransport{username: "key_secret", underlying: rec}
+
+	req := httptest.NewRequest(http.MethodGet, "https://api.cursor.com/teams/members", nil)
+	_, err := transport.RoundTrip(req)
+	require.NoError(t, err)
+
+	require.NotNil(t, rec.lastRequest)
+	user, pass, ok := rec.lastRequest.BasicAuth()
+	require.True(t, ok, "expected a Basic auth header")
+	assert.Equal(t, "key_secret", user)
+	assert.Empty(t, pass, "password must be empty")
+
+	// The original request must be left untouched (RoundTrip clones it).
+	_, _, originalHasAuth := req.BasicAuth()
+	assert.False(t, originalHasAuth, "original request must not be mutated")
+}
+
+func TestAPIKeyConnection_Client_BasicAuth(t *testing.T) {
+	t.Parallel()
+
+	conn := &APIKeyConnection{APIKey: "key_secret", BasicAuth: true}
+
+	client, err := conn.Client(context.Background())
+	require.NoError(t, err)
+
+	transport, ok := client.Transport.(*basicAuthTransport)
+	require.Truef(t, ok, "expected *basicAuthTransport, got %T", client.Transport)
+	assert.Equal(t, "key_secret", transport.username)
+}
+
+func TestAPIKeyConnection_Client_Header(t *testing.T) {
+	t.Parallel()
+
+	conn := &APIKeyConnection{APIKey: "sk-ant-admin", Header: "x-api-key"}
+
+	client, err := conn.Client(context.Background())
+	require.NoError(t, err)
+
+	transport, ok := client.Transport.(*apiKeyHeaderTransport)
+	require.Truef(t, ok, "expected *apiKeyHeaderTransport, got %T", client.Transport)
+	assert.Equal(t, "x-api-key", transport.header)
+	assert.Equal(t, "sk-ant-admin", transport.value)
+}
+
+func TestAPIKeyConnection_Client_BearerDefault(t *testing.T) {
+	t.Parallel()
+
+	conn := &APIKeyConnection{APIKey: "token"}
+
+	client, err := conn.Client(context.Background())
+	require.NoError(t, err)
+
+	transport, ok := client.Transport.(*oauth2Transport)
+	require.Truef(t, ok, "expected *oauth2Transport, got %T", client.Transport)
+	assert.Equal(t, "token", transport.token)
+}
diff --git a/pkg/connector/provider/registry.go b/pkg/connector/provider/registry.go
index 3a1a75ed8..85e2039cb 100644
--- a/pkg/connector/provider/registry.go
+++ b/pkg/connector/provider/registry.go
@@ -71,6 +71,13 @@ func (r *Registry) Register(reg *Registration) error {
 		return fmt.Errorf("cannot register connector provider %q: missing DisplayName", reg.Provider)
 	}
 
+	// APIKeyBasicAuth and APIKeyHeader select different presentations of
+	// the same key; setting both is a programmer error with a silent
+	// winner (Client checks BasicAuth first). Reject it at startup.
+	if reg.APIKeyBasicAuth && reg.APIKeyHeader != "" {
+		return fmt.Errorf("cannot register connector provider %q: APIKeyBasicAuth and APIKeyHeader are mutually exclusive", reg.Provider)
+	}
+
 	r.mu.Lock()
 	defer r.mu.Unlock()
 
@@ -132,6 +139,18 @@ func (r *Registry) APIKeyHeader(p coredata.ConnectorProvider) string {
 	return ""
 }
 
+// APIKeyUsesBasicAuth reports whether an API-key connection for the
+// given provider must present its key as an HTTP Basic auth username
+// (empty password) instead of a Bearer token. Returns false for unknown
+// providers and for providers that use the default Bearer scheme.
+func (r *Registry) APIKeyUsesBasicAuth(p coredata.ConnectorProvider) bool {
+	if reg, ok := r.Get(p); ok {
+		return reg.APIKeyBasicAuth
+	}
+
+	return false
+}
+
 // ProviderOAuth2Scopes returns the OAuth2 scopes the access review
 // driver for the given provider needs to list user accounts. Returns
 // nil for providers that do not need any scopes (Notion, Intercom)
diff --git a/pkg/connector/provider/registry_test.go b/pkg/connector/provider/registry_test.go
index d8e3fa2e5..c0759da85 100644
--- a/pkg/connector/provider/registry_test.go
+++ b/pkg/connector/provider/registry_test.go
@@ -81,6 +81,20 @@ func TestRegistry_Register(t *testing.T) {
 		assert.Contains(t, err.Error(), "missing DisplayName")
 	})
 
+	t.Run("APIKeyBasicAuth and APIKeyHeader mutually exclusive", func(t *testing.T) {
+		t.Parallel()
+
+		r := provider.NewRegistry()
+		err := r.Register(&provider.Registration{
+			Provider:        coredata.ConnectorProviderSlack,
+			DisplayName:     "Slack",
+			APIKeyBasicAuth: true,
+			APIKeyHeader:    "x-api-key",
+		})
+		require.Error(t, err)
+		assert.Contains(t, err.Error(), "mutually exclusive")
+	})
+
 	t.Run("duplicate registration", func(t *testing.T) {
 		t.Parallel()
 
diff --git a/pkg/connector/provider/types.go b/pkg/connector/provider/types.go
index 0c02b5d21..08f022927 100644
--- a/pkg/connector/provider/types.go
+++ b/pkg/connector/provider/types.go
@@ -63,6 +63,13 @@ type Registration struct {
 	// (Anthropic). It is consumed when the create-connector resolver
 	// builds the APIKeyConnection.
 	APIKeyHeader string
+	// APIKeyBasicAuth, when true, presents the API key as the username
+	// of an HTTP Basic credential with an empty password instead of a
+	// Bearer token — required by providers such as Cursor whose Admin
+	// API documents `-u <key>:` Basic auth. Mutually exclusive with
+	// APIKeyHeader. Consumed when the create-connector resolver builds
+	// the APIKeyConnection.
+	APIKeyBasicAuth bool
 
 	// Factory closures — wired by Stages 2 and 3.
 	NewDriver               func(context.Context, *http.Client, *coredata.Connector, *log.Logger) (drivers.Driver, error)
diff --git a/pkg/server/api/console/v1/connector_resolvers.go b/pkg/server/api/console/v1/connector_resolvers.go
index 7a164fcc0..b7e7d28c9 100644
--- a/pkg/server/api/console/v1/connector_resolvers.go
+++ b/pkg/server/api/console/v1/connector_resolvers.go
@@ -41,8 +41,9 @@ func (r *mutationResolver) CreateAPIKeyConnector(ctx context.Context, input type
 		Provider:       input.Provider,
 		Protocol:       coredata.ConnectorProtocolAPIKey,
 		Connection: &connector.APIKeyConnection{
-			APIKey: input.APIKey,
-			Header: r.providerRegistry.APIKeyHeader(input.Provider),
+			APIKey:    input.APIKey,
+			Header:    r.providerRegistry.APIKeyHeader(input.Provider),
+			BasicAuth: r.providerRegistry.APIKeyUsesBasicAuth(input.Provider),
 		},
 	}