diff --git a/changes/19512-mdm-migration-sonoma b/changes/19512-mdm-migration-sonoma
new file mode 100644
index 0000000000..d82dff2208
--- /dev/null
+++ b/changes/19512-mdm-migration-sonoma
@@ -0,0 +1 @@
+- Fixed bug where MDM migration failed when attempting to renew enrollment profiles on macOS Sonoma devices.
diff --git a/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx b/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx
index 3114d73530..2f40fa82b6 100644
--- a/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx
+++ b/frontend/pages/hosts/details/DeviceUserPage/AutoEnrollMdmModal/AutoEnrollMdmModal.tsx
@@ -2,16 +2,27 @@ import React from "react";
 
 import Button from "components/buttons/Button";
 import Modal from "components/Modal";
+import { IDeviceUserResponse } from "interfaces/host";
 
 interface IAutoEnrollMdmModalProps {
+  host: IDeviceUserResponse["host"];
   onCancel: () => void;
 }
 
 const baseClass = "auto-enroll-mdm-modal";
 
 const AutoEnrollMdmModal = ({
+  host: { platform, os_version },
   onCancel,
 }: IAutoEnrollMdmModalProps): JSX.Element => {
+  let isMacOsSonomaOrLater = false;
+  if (platform === "darwin" && os_version.startsWith("macOS ")) {
+    const [major] = os_version
+      .replace("macOS ", "")
+      .split(".")
+      .map((s) => parseInt(s, 10));
+    isMacOsSonomaOrLater = major >= 14;
+  }
   return (
     <Modal
       title="Turn on MDM"
@@ -25,13 +36,21 @@ const AutoEnrollMdmModal = ({
         </p>
         <ol>
           <li>
-            Open your Mac’s notification center by selecting the date and time
-            in the top right corner of your screen.
+            From the Apple menu in the top left corner of your screen, select{" "}
+            <b>System Settings</b> or <b>System Preferences</b>.
           </li>
           <li>
-            Select the <b>Device Enrollment</b> notification. This will open{" "}
-            <b>System Settings</b> or <b>System Preferences</b>. Select{" "}
-            <b>Allow</b>.
+            {isMacOsSonomaOrLater ? (
+              <>
+                In the sidebar menu, select <b>Enroll in Remote Management</b>,
+                and select <b>Enroll</b>.
+              </>
+            ) : (
+              <>
+                In the search bar, type “Profiles.” Select <b>Profiles</b>, find
+                and select <b>Enrollment Profile</b>, and select <b>Install</b>.
+              </>
+            )}
           </li>
           <li>
             Enter your password, and select <b>Enroll</b>.
diff --git a/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx b/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx
index d950153f48..16b38e11a8 100644
--- a/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx
+++ b/frontend/pages/hosts/details/DeviceUserPage/DeviceUserPage.tsx
@@ -311,7 +311,7 @@ const DeviceUserPage = ({
 
   const renderEnrollMdmModal = () => {
     return host?.dep_assigned_to_fleet ? (
-      <AutoEnrollMdmModal onCancel={toggleEnrollMdmModal} />
+      <AutoEnrollMdmModal host={host} onCancel={toggleEnrollMdmModal} />
     ) : (
       <ManualEnrollMdmModal
         onCancel={toggleEnrollMdmModal}
diff --git a/orbit/pkg/profiles/profiles_darwin.go b/orbit/pkg/profiles/profiles_darwin.go
index b530e15b19..93d197a587 100644
--- a/orbit/pkg/profiles/profiles_darwin.go
+++ b/orbit/pkg/profiles/profiles_darwin.go
@@ -247,6 +247,6 @@ func parseEnrollmentProfileValue(line []byte, key string) (string, bool) {
 
 // showEnrollmentProfileCmd is declared as a variable so it can be overwritten by tests.
 var showEnrollmentProfileCmd = func() ([]byte, error) {
-	cmd := exec.Command("/usr/bin/profiles", "show", "-type", "enrollment")
+	cmd := exec.Command("sh", "-c", `launchctl asuser $(id -u $(stat -f "%u" /dev/console)) profiles show -type enrollment`)
 	return cmd.Output()
 }
diff --git a/orbit/pkg/update/execcmd_darwin.go b/orbit/pkg/update/execcmd_darwin.go
index 65cbdf7c27..6eb8847282 100644
--- a/orbit/pkg/update/execcmd_darwin.go
+++ b/orbit/pkg/update/execcmd_darwin.go
@@ -3,5 +3,6 @@
 package update
 
 func runRenewEnrollmentProfile() error {
-	return runCmdCollectErr("/usr/bin/profiles", "renew", "--type", "enrollment")
+	cmd := `launchctl asuser $(id -u $(stat -f "%u" /dev/console)) profiles renew -type enrollment`
+	return runCmdCollectErr("sh", "-c", cmd)
 }
diff --git a/orbit/pkg/update/notifications.go b/orbit/pkg/update/notifications.go
index c185ee64bd..63224ac859 100644
--- a/orbit/pkg/update/notifications.go
+++ b/orbit/pkg/update/notifications.go
@@ -104,14 +104,15 @@ func (h *renewEnrollmentProfileConfigReceiver) Run(config *fleet.OrbitConfig) er
 					fn = runRenewEnrollmentProfile
 				}
 				if err := fn(); err != nil {
-					// TODO: Look into whether we should increment lastRun here or implement a
-					// backoff to avoid unnecessary user notification popups and mitigate rate
-					// limiting by Apple.
 					log.Info().Err(err).Msg("calling /usr/bin/profiles to renew enrollment profile failed")
-				} else {
-					h.lastRun = time.Now()
-					log.Info().Msg("successfully called /usr/bin/profiles to renew enrollment profile")
+					// TODO: Design a better way to backoff `profiles show` so that the device doesn't get rate
+					// limited by Apple. For now, wait at least 2 minutes before retrying.
+					h.lastRun = time.Now().Add(-h.Frequency).Add(2 * time.Minute)
+					return nil
 				}
+				h.lastRun = time.Now()
+				log.Info().Msg("successfully called /usr/bin/profiles to renew enrollment profile")
+
 			} else {
 				log.Debug().Msg("skipped calling /usr/bin/profiles to renew enrollment profile, last run was too recent")
 			}
diff --git a/orbit/pkg/useraction/mdm_migration_darwin.go b/orbit/pkg/useraction/mdm_migration_darwin.go
index a282a9a05c..323fc847fa 100644
--- a/orbit/pkg/useraction/mdm_migration_darwin.go
+++ b/orbit/pkg/useraction/mdm_migration_darwin.go
@@ -8,6 +8,8 @@ import (
 	"fmt"
 	"os"
 	"os/exec"
+	"strconv"
+	"strings"
 	"sync"
 	"text/template"
 	"time"
@@ -48,7 +50,7 @@ const mdmUnenrollmentTotalWaitTime = 90 * time.Second
 // between unenrollment checks.
 const defaultUnenrollmentRetryInterval = 5 * time.Second
 
-var mdmMigrationTemplate = template.Must(template.New("mdmMigrationTemplate").Parse(`
+var mdmMigrationTemplatePreSonoma = template.Must(template.New("mdmMigrationTemplate").Parse(`
 ## Migrate to Fleet
 
 Select **Start** and look for this notification in your notification center:` +
@@ -56,6 +58,14 @@ Select **Start** and look for this notification in your notification center:` +
 	"After you start, this window will popup every 15-20 minutes until you finish.",
 ))
 
+var mdmMigrationTemplate = template.Must(template.New("mdmMigrationTemplate").Parse(`
+## Migrate to Fleet
+
+Select **Start** and Remote Management window will appear soon:` +
+	"\n\n![Image showing MDM migration notification](https://fleetdm.com/images/permanent/mdm-migration-sonoma-1500x938.png)\n\n" +
+	"After you start, this window will popup every 15-20 minutes until you finish.",
+))
+
 var errorTemplate = template.Must(template.New("").Parse(`
 ### Something's gone wrong.
 
@@ -291,29 +301,9 @@ func (m *swiftDialogMDMMigrator) waitForUnenrollment() error {
 }
 
 func (m *swiftDialogMDMMigrator) renderMigration() error {
-	var message bytes.Buffer
-	if err := mdmMigrationTemplate.Execute(
-		&message,
-		m.props,
-	); err != nil {
-		return fmt.Errorf("execute template: %w", err)
-	}
-
-	flags := []string{
-		// main button
-		"--button1text", "Start",
-		// secondary button
-		"--button2text", "Later",
-		"--height", "440",
-	}
-
-	if m.props.OrgInfo.ContactURL != "" {
-		flags = append(flags,
-			// info button
-			"--infobuttontext", "Unsure? Contact IT",
-			"--infobuttonaction", m.props.OrgInfo.ContactURL,
-			"--quitoninfo",
-		)
+	message, flags, err := m.getMessageAndFlags()
+	if err != nil {
+		return fmt.Errorf("getting mdm migrator message: %w", err)
 	}
 
 	exitCodeCh, errCh := m.render(message.String(), flags...)
@@ -419,3 +409,71 @@ func (m *swiftDialogMDMMigrator) ShowInterval() error {
 func (m *swiftDialogMDMMigrator) SetProps(props MDMMigratorProps) {
 	m.props = props
 }
+
+func (m *swiftDialogMDMMigrator) getMessageAndFlags() (*bytes.Buffer, []string, error) {
+	vers, err := m.getMacOSMajorVersion()
+	if err != nil {
+		// log error for debugging and continue with default template
+		log.Error().Err(err).Msg("getting macOS major version failed: using default migration template")
+	}
+
+	tmpl := mdmMigrationTemplate
+	height := "669"
+	if vers != 0 && vers < 14 {
+		height = "440"
+		tmpl = mdmMigrationTemplatePreSonoma
+	}
+
+	var message bytes.Buffer
+	if err := tmpl.Execute(
+		&message,
+		m.props,
+	); err != nil {
+		return nil, nil, fmt.Errorf("executing migrqation template: %w", err)
+	}
+
+	flags := []string{
+		// main button
+		"--button1text", "Start",
+		// secondary button
+		"--button2text", "Later",
+		"--height", height,
+	}
+
+	if m.props.OrgInfo.ContactURL != "" {
+		flags = append(flags,
+			// info button
+			"--infobuttontext", "Unsure? Contact IT",
+			"--infobuttonaction", m.props.OrgInfo.ContactURL,
+			"--quitoninfo",
+		)
+	}
+
+	return &message, flags, nil
+}
+
+// TODO: make this a variable for testing
+func (m *swiftDialogMDMMigrator) getMacOSMajorVersion() (int, error) {
+	cmd := exec.Command("sw_vers", "-productVersion")
+	out, err := cmd.Output()
+	if err != nil {
+		return 0, fmt.Errorf("getting macOS version: %w", err)
+	}
+	parts := strings.SplitN(string(out), ".", 2)
+	switch len(parts) {
+	case 0:
+		// this should never happen
+		return 0, errors.New("getting macOS version: sw_vers command returned no output")
+	case 1:
+		// unexpected, so log for debugging
+		log.Debug().Msgf("parsing macOS version: expected 2 parts, got 1: %s", out)
+	default:
+		// ok
+	}
+
+	major, err := strconv.Atoi(parts[0])
+	if err != nil {
+		return 0, fmt.Errorf("parsing macOS major version: %w", err)
+	}
+	return major, nil
+}
diff --git a/website/assets/images/permanent/mdm-migration-sonoma-1500x938.png b/website/assets/images/permanent/mdm-migration-sonoma-1500x938.png
new file mode 100644
index 0000000000..494d04ea3c
Binary files /dev/null and b/website/assets/images/permanent/mdm-migration-sonoma-1500x938.png differ