diff --git a/src/backend/database/routes/host-normalizers.ts b/src/backend/database/routes/host-normalizers.ts
index 510198ad..eb0ce4b1 100644
--- a/src/backend/database/routes/host-normalizers.ts
+++ b/src/backend/database/routes/host-normalizers.ts
@@ -346,6 +346,7 @@ const CONNECT_LEVEL_FIELDS = new Set([
   "enableTelnet",
   "sshPort",
   "rdpPort",
+  "rdpAuthType",
   "vncPort",
   "telnetPort",
   "defaultPath",
diff --git a/src/backend/hosts/guacamole/rdp-settings.ts b/src/backend/hosts/guacamole/rdp-settings.ts
index 63ada8e1..305c153c 100644
--- a/src/backend/hosts/guacamole/rdp-settings.ts
+++ b/src/backend/hosts/guacamole/rdp-settings.ts
@@ -34,3 +34,31 @@ export function resolveRdpDomain(
     ? promptedDomain
     : storedDomain;
 }
+
+type SharedRdpAuthResolution =
+  | { source: "personal-override" }
+  | { source: "owner-shared"; authType: string }
+  | { source: "secretless" }
+  | { source: "required" }
+  | null;
+
+export function resolveRdpAuthTypeForConnect({
+  storedAuthType,
+  credentialId,
+  sharedResolution,
+}: {
+  storedAuthType?: string | null;
+  credentialId?: number | null;
+  sharedResolution?: SharedRdpAuthResolution;
+}): string {
+  if (sharedResolution === undefined) {
+    return storedAuthType || (credentialId ? "credential" : "direct");
+  }
+  if (sharedResolution?.source === "personal-override") return "credential";
+  if (sharedResolution?.source === "owner-shared") {
+    return sharedResolution.authType;
+  }
+  return sharedResolution?.source === "secretless" && storedAuthType === "none"
+    ? "none"
+    : "direct";
+}
diff --git a/src/backend/hosts/guacamole/routes.ts b/src/backend/hosts/guacamole/routes.ts
index e5374eda..c8634d90 100644
--- a/src/backend/hosts/guacamole/routes.ts
+++ b/src/backend/hosts/guacamole/routes.ts
@@ -6,7 +6,10 @@ import { withDriveSettings } from "./drive-settings.js";
 import { guacLogger } from "../../utils/logger.js";
 import { AuthManager } from "../../utils/auth-manager.js";
 import { PermissionManager } from "../../utils/permission-manager.js";
-import { resolveRecipientSharedHostAuthentication } from "../../utils/shared-host-auth-resolver.js";
+import {
+  resolveRecipientSharedHostAuthentication,
+  type RecipientSharedHostAuthResolution,
+} from "../../utils/shared-host-auth-resolver.js";
 import type { AuthOverrideProtocol } from "../../../types/auth-protocols.js";
 import net from "net";
 import crypto from "crypto";
@@ -25,7 +28,11 @@ import {
   getRequestMeta,
 } from "../../utils/audit-logger.js";
 import { resolveJumpTunnelEndpoint } from "./jump-tunnel-endpoint.js";
-import { buildRdpSettings, resolveRdpDomain } from "./rdp-settings.js";
+import {
+  buildRdpSettings,
+  resolveRdpAuthTypeForConnect,
+  resolveRdpDomain,
+} from "./rdp-settings.js";
 import { createMacosVncCompatibilityProxy } from "./macos-vnc-proxy.js";
 
 const router = express.Router();
@@ -322,6 +329,7 @@ router.post(
       const hostRecord = host as Record<string, unknown>;
       const hostRepository = hostResolutionRepository;
       const isSharedConnection = host.userId !== userId;
+      let sharedAuthResolution: RecipientSharedHostAuthResolution | null = null;
 
       if (isSharedConnection) {
         // Recipients never read the owner's raw secrets; wipe them and use
@@ -341,6 +349,7 @@ router.post(
             userId,
             connectionType as AuthOverrideProtocol,
           );
+          sharedAuthResolution = resolution;
           const auth =
             resolution.source === "personal-override"
               ? { ...resolution.credential, domain: null }
@@ -448,10 +457,11 @@ router.post(
       let username: string;
       let password: string;
 
-      const rdpAuthTypeForConnect = isSharedConnection
-        ? null
-        : (host.rdpAuthType as string) ||
-          (host.rdpCredentialId ? "credential" : "direct");
+      const rdpAuthTypeForConnect = resolveRdpAuthTypeForConnect({
+        storedAuthType: host.rdpAuthType as string | null,
+        credentialId: host.rdpCredentialId as number | null,
+        sharedResolution: isSharedConnection ? sharedAuthResolution : undefined,
+      });
 
       switch (connectionType) {
         case "rdp":
diff --git a/src/backend/tests/database/routes/host-normalizers.test.ts b/src/backend/tests/database/routes/host-normalizers.test.ts
index c489cc45..50939dbc 100644
--- a/src/backend/tests/database/routes/host-normalizers.test.ts
+++ b/src/backend/tests/database/routes/host-normalizers.test.ts
@@ -394,6 +394,7 @@ describe("sanitizeHostForRecipient", () => {
       {
         ...sharedHost,
         permissionLevel: "connect",
+        rdpAuthType: "none",
         authOverrides: {
           ssh: {
             credentialId: 9,
@@ -408,6 +409,7 @@ describe("sanitizeHostForRecipient", () => {
     expect(result.ip).toBe("10.0.0.42");
     expect(result.enableRdp).toBe(true);
     expect(result.rdpPort).toBe(3389);
+    expect(result.rdpAuthType).toBe("none");
     expect(result.permissionLevel).toBe("connect");
     expect(result.shareSshAuth).toBe(true);
     expect(result.authOverrides).toEqual({
diff --git a/src/backend/tests/hosts/guacamole/rdp-settings.test.ts b/src/backend/tests/hosts/guacamole/rdp-settings.test.ts
index 193c0414..d945a839 100644
--- a/src/backend/tests/hosts/guacamole/rdp-settings.test.ts
+++ b/src/backend/tests/hosts/guacamole/rdp-settings.test.ts
@@ -1,6 +1,7 @@
 import { describe, expect, it } from "vitest";
 import {
   buildRdpSettings,
+  resolveRdpAuthTypeForConnect,
   resolveRdpDomain,
 } from "../../../hosts/guacamole/rdp-settings.js";
 
@@ -52,3 +53,32 @@ describe("buildRdpSettings", () => {
     expect(resolveRdpDomain("none", undefined, "SAVED")).toBe("SAVED");
   });
 });
+
+describe("resolveRdpAuthTypeForConnect", () => {
+  it("keeps prompt-on-connect authentication for a secretless recipient", () => {
+    expect(
+      resolveRdpAuthTypeForConnect({
+        storedAuthType: "none",
+        sharedResolution: { source: "secretless" },
+      }),
+    ).toBe("none");
+  });
+
+  it("uses a recipient override instead of prompting", () => {
+    expect(
+      resolveRdpAuthTypeForConnect({
+        storedAuthType: "none",
+        sharedResolution: { source: "personal-override" },
+      }),
+    ).toBe("credential");
+  });
+
+  it("uses authentication shared by the owner", () => {
+    expect(
+      resolveRdpAuthTypeForConnect({
+        storedAuthType: "credential",
+        sharedResolution: { source: "owner-shared", authType: "credential" },
+      }),
+    ).toBe("credential");
+  });
+});
diff --git a/src/ui/features/guacamole/GuacamoleApp.tsx b/src/ui/features/guacamole/GuacamoleApp.tsx
index 223dcfa0..eb6f2758 100644
--- a/src/ui/features/guacamole/GuacamoleApp.tsx
+++ b/src/ui/features/guacamole/GuacamoleApp.tsx
@@ -46,6 +46,7 @@ import { ShareSessionModal } from "@/features/session-sharing/ShareSessionModal.
 import type { SSHHost } from "@/types";
 import { useConnectionDefaults } from "@/contexts/ConnectionDefaultsContext";
 import { resolveConnectionDefaults } from "@/lib/connection-defaults";
+import { needsRdpCredentialPrompt } from "@/features/guacamole/rdp-credential-prompt";
 
 interface GuacamoleAppProps {
   hostId?: string;
@@ -162,6 +163,7 @@ interface GuacamoleAppInnerProps {
     | "domain"
     | "guacamoleConfig"
     | "rdpAuthType"
+    | "authOverrides"
     | "syncId"
     | "ip"
     | "rdpPort"
@@ -230,8 +232,11 @@ const GuacamoleAppInner = React.forwardRef<
   const resolvedProtocolForConnect = (protocol ??
     hostConfig.connectionType ??
     "rdp") as "rdp" | "vnc" | "telnet";
-  const needsCredentialPrompt =
-    resolvedProtocolForConnect === "rdp" && hostConfig.rdpAuthType === "none";
+  const needsCredentialPrompt = needsRdpCredentialPrompt({
+    protocol: resolvedProtocolForConnect,
+    rdpAuthType: hostConfig.rdpAuthType,
+    authOverrides: hostConfig.authOverrides,
+  });
 
   const [promptedCredentials, setPromptedCredentials] = useState<{
     username: string;
diff --git a/src/ui/features/guacamole/rdp-credential-prompt.ts b/src/ui/features/guacamole/rdp-credential-prompt.ts
new file mode 100644
index 00000000..746e5ffa
--- /dev/null
+++ b/src/ui/features/guacamole/rdp-credential-prompt.ts
@@ -0,0 +1,17 @@
+import type { HostAuthOverrides } from "@/types/auth-protocols";
+
+export function needsRdpCredentialPrompt({
+  protocol,
+  rdpAuthType,
+  authOverrides,
+}: {
+  protocol: "rdp" | "vnc" | "telnet";
+  rdpAuthType?: string;
+  authOverrides?: HostAuthOverrides;
+}): boolean {
+  return (
+    protocol === "rdp" &&
+    rdpAuthType === "none" &&
+    !authOverrides?.rdp?.credentialId
+  );
+}
diff --git a/src/ui/tests/features/guacamole/rdp-credential-prompt.test.ts b/src/ui/tests/features/guacamole/rdp-credential-prompt.test.ts
new file mode 100644
index 00000000..ff892683
--- /dev/null
+++ b/src/ui/tests/features/guacamole/rdp-credential-prompt.test.ts
@@ -0,0 +1,28 @@
+import { describe, expect, it } from "vitest";
+import { needsRdpCredentialPrompt } from "@/features/guacamole/rdp-credential-prompt";
+
+describe("needsRdpCredentialPrompt", () => {
+  it("prompts recipients when RDP has no saved authentication", () => {
+    expect(
+      needsRdpCredentialPrompt({ protocol: "rdp", rdpAuthType: "none" }),
+    ).toBe(true);
+  });
+
+  it("does not prompt when the recipient has a personal override", () => {
+    expect(
+      needsRdpCredentialPrompt({
+        protocol: "rdp",
+        rdpAuthType: "none",
+        authOverrides: {
+          rdp: { credentialId: 7, required: false, ownerAuthShared: true },
+        },
+      }),
+    ).toBe(false);
+  });
+
+  it("does not prompt for other protocols", () => {
+    expect(
+      needsRdpCredentialPrompt({ protocol: "vnc", rdpAuthType: "none" }),
+    ).toBe(false);
+  });
+});