diff --git a/changes/43379-windows-mdm-end-user-experience-labels b/changes/43379-windows-mdm-end-user-experience-labels
new file mode 100644
index 0000000000..67db94cc29
--- /dev/null
+++ b/changes/43379-windows-mdm-end-user-experience-labels
@@ -0,0 +1 @@
+- Updated Windows MDM end user experience radio button labels from Automatic/Manual to Fleet agent-driven/End user-driven to reduce confusion with MDM status terminology.
diff --git a/docs/Configuration/yaml-files.md b/docs/Configuration/yaml-files.md
index 550d3a4ba0..4e923f9966 100644
--- a/docs/Configuration/yaml-files.md
+++ b/docs/Configuration/yaml-files.md
@@ -346,7 +346,7 @@ The `controls` section allows you to configure scripts and device management (MD
 - `windows_enabled_and_configured` specifies whether or not to turn on Windows MDM features (default: `false`). Can only be configured for "All fleets" (`default.yml`).
 - `windows_entra_tenant_ids` is a list of Microsoft Entra tenant IDs to enable automatic (Autopilot) and manual enrollment by end users (**Settings** > **Accounts** > **Access work or school** on Windows). Can only be configured for "All fleets" (`default.yml`). Find your **Tenant ID**, on [**Microsoft Entra ID** > **Home**](https://entra.microsoft.com/#home).
 - `windows_entra_client_ids` is a list of Microsoft Entra application (client) IDs for the applications used to enroll Windows hosts via Microsoft Entra. Set this when you set up Entra enrollment: Microsoft Entra issues v2 access tokens whose audience is the application's client ID, so Fleet needs the client ID to authorize enrollment. Can only be configured for "All fleets" (`default.yml`). Find your **Application (client) ID** on [**Microsoft Entra ID** > **App registrations**](https://entra.microsoft.com/#view/Microsoft_AAD_RegisteredApps/ApplicationsListBlade) > your MDM application > **Overview**.
-- `enable_turn_on_windows_mdm_manually` specifies whether or not to require end users to manually turn on MDM in **Settings > Access work or school** (default: `false`). If `false`, MDM is automatically turned on for all Windows hosts that aren't connected to any MDM solution. Can only be configured for "All fleets" (`default.yml`).
+- `enable_turn_on_windows_mdm_manually` specifies whether or not to require end users to sign in using **Settings > Access work or school** (default: `false`). If `false`, MDM is automatically turned on for all Windows hosts that aren't connected to any MDM solution. Either method results in an MDM status of "On (manual)". To get a status of "On (company-owned)", use [Windows Autopilot](https://fleetdm.com/guides/windows-mdm-setup#windows-autopilot). Can only be configured for "All fleets" (`default.yml`).
 - `windows_migration_enabled` specifies whether or not to automatically migrate Windows hosts connected to another MDM solution. If `false`, MDM is only turned on after hosts are unenrolled from your old MDM solution. `enable_turn_on_windows_mdm_manually` must be set to `false`. (default: `false`). Can only be configured for "All fleets" (`default.yml`).
 - `enable_disk_encryption` specifies whether or not to enforce disk encryption on macOS, Windows, and Linux hosts (default: `false`).
 - `windows_require_bitlocker_pin` specifies whether or not to require end users on Windows hosts to set a BitLocker PIN. When set, this PIN is required to unlock Windows host during startup. `enable_disk_encryption` must be set to `true`. (default: `false`).
diff --git a/frontend/components/forms/fields/Radio/_styles.scss b/frontend/components/forms/fields/Radio/_styles.scss
index b3c42f3f06..757a7036e0 100644
--- a/frontend/components/forms/fields/Radio/_styles.scss
+++ b/frontend/components/forms/fields/Radio/_styles.scss
@@ -73,7 +73,6 @@
   &__help-text {
     @include help-text;
     margin-top: $pad-xxsmall;
-    margin-left: calc(20px + #{$pad-small});
   }
 
   &__disabled {
diff --git a/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tests.tsx b/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tests.tsx
index d2b54f0096..c80467a078 100644
--- a/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tests.tsx
+++ b/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tests.tsx
@@ -21,15 +21,13 @@ describe("WindowsMdmPage", () => {
 
     // switch and description only shown
     expect(screen.getByRole("switch")).toBeInTheDocument();
-    expect(
-      screen.getByText(
-        "Turns on MDM for Windows hosts that enroll to Fleet (excluding servers)."
-      )
-    ).toBeInTheDocument();
+    expect(screen.getByText(/On \(manual\)/)).toBeInTheDocument();
 
     // no end user experience form
-    expect(screen.queryByLabelText("Automatic")).not.toBeInTheDocument();
-    expect(screen.queryByLabelText("Manual")).not.toBeInTheDocument();
+    expect(
+      screen.queryByLabelText("Fleet agent-driven")
+    ).not.toBeInTheDocument();
+    expect(screen.queryByLabelText("End user-driven")).not.toBeInTheDocument();
   });
 
   it("renders the end user experience form as disabled when MDM is off", () => {
@@ -46,8 +44,8 @@ describe("WindowsMdmPage", () => {
 
     render(<WindowsMdmPage router={createMockRouter()} />);
 
-    expect(screen.getByLabelText("Automatic")).toBeDisabled();
-    expect(screen.getByLabelText("Manual")).toBeDisabled();
+    expect(screen.getByLabelText("Fleet agent-driven")).toBeDisabled();
+    expect(screen.getByLabelText("End user-driven")).toBeDisabled();
   });
 
   it("renders the automatically migrate checkbox if automatic mdm enrollment is selected", () => {
@@ -67,8 +65,8 @@ describe("WindowsMdmPage", () => {
 
     render(<WindowsMdmPage router={createMockRouter()} />);
 
-    // automatic is selected and the checkbox is visible
-    expect(screen.getByLabelText("Automatic")).toBeChecked();
+    // Fleet agent-driven is selected and the checkbox is visible
+    expect(screen.getByLabelText("Fleet agent-driven")).toBeChecked();
     expect(screen.getByRole("checkbox")).toBeVisible();
   });
 });
diff --git a/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tsx b/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tsx
index a265267f53..60d97abe01 100644
--- a/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tsx
+++ b/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/WindowsMdmPage.tsx
@@ -110,10 +110,6 @@ const WindowsMdmPage = ({ router }: IWindowsMdmPageProps) => {
     updateWindowsMdm();
   };
 
-  const descriptionText = mdmOn
-    ? "Turns on MDM for Windows hosts that enroll to Fleet (excluding servers)."
-    : "Hosts with MDM already turned on will not have MDM removed.";
-
   return (
     <MainContent className={baseClass}>
       <>
@@ -126,6 +122,16 @@ const WindowsMdmPage = ({ router }: IWindowsMdmPageProps) => {
         </div>
         <h1>Windows MDM</h1>
         <form>
+          <p>
+            Hosts that turn on MDM manually will have a status of &quot;On
+            (manual)&quot;. To get a status of &quot;On (company-owned)&quot;,
+            use{" "}
+            <CustomLink
+              text="Windows Autopilot."
+              url="https://fleetdm.com/guides/windows-mdm-setup#windows-autopilot"
+              newTab
+            />
+          </p>
           <Slider
             value={mdmOn}
             activeText="Windows MDM on"
@@ -133,7 +139,6 @@ const WindowsMdmPage = ({ router }: IWindowsMdmPageProps) => {
             onChange={onChangeMdmOn}
             disabled={gitOpsModeEnabled}
           />
-          {!isPremiumTier && <p>{descriptionText}</p>}
           {isPremiumTier && (
             // NOTE: first time using fieldset and legend. if we use this more we should make
             // a reusable component
@@ -147,7 +152,7 @@ const WindowsMdmPage = ({ router }: IWindowsMdmPageProps) => {
               </div>
               <Radio
                 id="automatic-enrollment"
-                label="Automatic"
+                label="Fleet agent-driven"
                 value="automaticEnrollment"
                 name="enrollmentType"
                 checked={enrollmentType === "automatic"}
@@ -157,7 +162,7 @@ const WindowsMdmPage = ({ router }: IWindowsMdmPageProps) => {
               />
               <Radio
                 id="manual-enrollment"
-                label="Manual"
+                label="End user-driven"
                 value="manualEnrollment"
                 name="enrollmentType"
                 checked={enrollmentType === "manual"}
@@ -172,7 +177,7 @@ const WindowsMdmPage = ({ router }: IWindowsMdmPageProps) => {
                         PATHS.ADMIN_INTEGRATIONS_AUTOMATIC_ENROLLMENT_WINDOWS
                       }
                     />{" "}
-                    End users have to manually turn on MDM in{" "}
+                    End users have to sign in using{" "}
                     <b>Settings &gt; Access work or school.</b>
                   </>
                 }
diff --git a/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/__styles.scss b/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/__styles.scss
index 6dfca27f9f..9b9bb0b756 100644
--- a/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/__styles.scss
+++ b/frontend/pages/admin/IntegrationsPage/cards/MdmSettings/WindowsMdmPage/__styles.scss
@@ -4,4 +4,9 @@
   form {
     @include vertical-form-layout;
   }
+
+  .form-field__label {
+    font-size: $small;
+    margin-bottom: $pad-small;
+  }
 }