diff --git a/changes/27501-clear-windows-mdm-info-on-linux-enroll b/changes/27501-clear-windows-mdm-info-on-linux-enroll
new file mode 100644
index 0000000000..70f3173be4
--- /dev/null
+++ b/changes/27501-clear-windows-mdm-info-on-linux-enroll
@@ -0,0 +1 @@
+Windows hosts which re-enroll as another OS such as Linux will no longer show Windows MDM information on the hosts page unless they later re-enroll as a Windows host again(i.e. when dual booting).
diff --git a/server/datastore/mysql/hosts.go b/server/datastore/mysql/hosts.go
index bded5cb7ac..47412b355b 100644
--- a/server/datastore/mysql/hosts.go
+++ b/server/datastore/mysql/hosts.go
@@ -1859,6 +1859,8 @@ type enrolledHostInfo struct {
 	// NodeKeySet indicates whether `node_key` is set (NOT NULL) for a osquery host
 	// or if `orbit_node_key` is set (NOT NULL) for a orbit host.
 	NodeKeySet bool
+	// Platform is the OS of the host.
+	Platform string
 }
 
 // Attempts to find the matching host ID by osqueryID, host UUID or serial
@@ -1887,6 +1889,7 @@ func matchHostDuringEnrollment(
 		LastEnrolledAt time.Time `db:"last_enrolled_at"`
 		NodeKeySet     bool      `db:"node_key_set"`
 		Priority       int
+		Platform       string `db:"platform"`
 	}
 
 	var (
@@ -1902,7 +1905,7 @@ func matchHostDuringEnrollment(
 	}
 
 	if osqueryID != "" || uuid != "" {
-		_, _ = query.WriteString(fmt.Sprintf(`(SELECT id, last_enrolled_at, %s IS NOT NULL AS node_key_set, 1 priority FROM hosts WHERE osquery_host_id = ?)`, nodeKeyColumn))
+		_, _ = query.WriteString(fmt.Sprintf(`(SELECT id, last_enrolled_at, %s IS NOT NULL AS node_key_set, 1 priority, platform FROM hosts WHERE osquery_host_id = ?)`, nodeKeyColumn))
 		osqueryHostID := osqueryID
 		if osqueryID == "" {
 			// special-case, if there's no osquery identifier, use the uuid
@@ -1918,7 +1921,7 @@ func matchHostDuringEnrollment(
 		if query.Len() > 0 {
 			_, _ = query.WriteString(" UNION ")
 		}
-		_, _ = query.WriteString(fmt.Sprintf(`(SELECT id, last_enrolled_at, %s IS NOT NULL AS node_key_set, 2 priority FROM hosts WHERE hardware_serial = ? AND (platform = 'darwin' OR platform = 'ios' OR platform = 'ipados') ORDER BY id LIMIT 1)`, nodeKeyColumn))
+		_, _ = query.WriteString(fmt.Sprintf(`(SELECT id, last_enrolled_at, %s IS NOT NULL AS node_key_set, 2 priority, platform FROM hosts WHERE hardware_serial = ? AND (platform = 'darwin' OR platform = 'ios' OR platform = 'ipados') ORDER BY id LIMIT 1)`, nodeKeyColumn))
 		args = append(args, serial)
 	}
 
@@ -1936,6 +1939,7 @@ func matchHostDuringEnrollment(
 		ID:             rows[0].ID,
 		LastEnrolledAt: rows[0].LastEnrolledAt,
 		NodeKeySet:     rows[0].NodeKeySet,
+		Platform:       rows[0].Platform,
 	}, nil
 }
 
@@ -2015,6 +2019,14 @@ func (ds *Datastore) EnrollOrbit(ctx context.Context, isMDMEnabled bool, hostInf
 				return ctxerr.Wrap(ctx, err, "orbit enroll error clearing host_mdm_actions")
 			}
 
+			// Clear host_mdm table row for this host if switching from Windows to non-Windows(e.g. Ubuntu) platform
+			// so that hosts that get re-imaged with other OS don't show erroneous MDM status
+			if enrolledHostInfo.Platform == "windows" && hostInfo.Platform != "" && hostInfo.Platform != "windows" {
+				if _, err := tx.ExecContext(ctx, `DELETE FROM host_mdm WHERE host_id = ?`, enrolledHostInfo.ID); err != nil {
+					return ctxerr.Wrap(ctx, err, "orbit enroll error clearing host_mdm entry on platform change re-enrollment")
+				}
+			}
+
 		case errors.Is(err, sql.ErrNoRows):
 			zeroTime := time.Unix(0, 0).Add(24 * time.Hour)
 			// Create new host record. We always create newly enrolled hosts with refetch_requested = true
diff --git a/server/datastore/mysql/hosts_test.go b/server/datastore/mysql/hosts_test.go
index 85efd52a35..3bbd473d39 100644
--- a/server/datastore/mysql/hosts_test.go
+++ b/server/datastore/mysql/hosts_test.go
@@ -8848,6 +8848,90 @@ func testHostsEnrollOrbit(t *testing.T, ds *Datastore) {
 			scenarioD(platform)
 		})
 	}
+
+	// Scenario E:
+	//	- Fleet with MDM enabled.
+	// 	- two hosts with the same hardware identifiers (e.g. two cloned VMs) but platform may be different
+	//	- fleetd running with host identifier set to uuid (default).
+	//	- orbit enrolls first, then osquery
+	//  - host_mdm entry exists after first host enrolls
+	// Expected output: The two fleetd instances should be enrolled as one host and if the first host was
+	//   platform="windows" and the second host was not, the host_mdm entry should be removed
+	scenarioE := func(fromPlatform, toPlatform string) {
+		dupUUID := uuid.New().String()
+		dupHWSerial := uuid.New().String()
+
+		h1Orbit, err := ds.EnrollOrbit(ctx, false, fleet.OrbitHostInfo{
+			HardwareUUID:   dupUUID,
+			HardwareSerial: dupHWSerial,
+			Platform:       fromPlatform,
+		}, uuid.New().String(), nil)
+		require.NoError(t, err)
+		h1OrbitFetched, err := ds.Host(ctx, h1Orbit.ID)
+		require.NoError(t, err)
+		time.Sleep(1 * time.Second) // to test the update of last_enrolled_at
+		h1Osquery, err := ds.EnrollHost(ctx, false, dupUUID, dupUUID, dupHWSerial, uuid.New().String(), nil, 0)
+		require.NoError(t, err)
+		h1OsqueryFetched, err := ds.Host(ctx, h1Osquery.ID)
+		require.NoError(t, err)
+		require.NotEqual(t, h1OrbitFetched.LastEnrolledAt, h1OsqueryFetched.LastEnrolledAt)
+		require.Equal(t, h1Orbit.ID, h1Osquery.ID)
+		time.Sleep(1 * time.Second) // to test the update of last_enrolled_at
+
+		ExecAdhocSQL(t, ds, func(q sqlx.ExtContext) error {
+			_, err := q.ExecContext(ctx, `INSERT INTO host_mdm(host_id, enrolled, server_url, installed_from_dep, mdm_id, is_server)
+		VALUES(?, 1, 'https://example.com/mdm', 0, ?, 0)`, h1Orbit.ID, h1Orbit.ID+100)
+			return err
+		})
+		h1WithMdmFetched, err := ds.Host(ctx, h1Orbit.ID)
+		require.NoError(t, err)
+		require.NotNil(t, h1WithMdmFetched.MDM.ServerURL)
+		require.NotNil(t, h1WithMdmFetched.MDM.EnrollmentStatus)
+
+		h2Orbit, err := ds.EnrollOrbit(ctx, false, fleet.OrbitHostInfo{
+			HardwareUUID:   dupUUID,
+			HardwareSerial: dupHWSerial,
+			Platform:       toPlatform,
+		}, uuid.New().String(), nil)
+		require.NoError(t, err)
+		h2OrbitFetched, err := ds.Host(ctx, h2Orbit.ID)
+		require.NoError(t, err)
+		// orbit should not update last_enrolled_at if re-enrolling (because last_enrolled_at
+		// is to be set by osquery only).
+		require.Equal(t, h1OsqueryFetched.LastEnrolledAt, h2OrbitFetched.LastEnrolledAt)
+		time.Sleep(1 * time.Second) // to test the update of last_enrolled_at
+		h2Osquery, err := ds.EnrollHost(ctx, false, dupUUID, dupUUID, dupHWSerial, uuid.New().String(), nil, 0)
+		require.NoError(t, err)
+		require.Equal(t, h2Orbit.ID, h2Osquery.ID)
+		h2OsqueryFetched, err := ds.Host(ctx, h2Osquery.ID)
+		require.NoError(t, err)
+		require.NotEqual(t, h2OrbitFetched.LastEnrolledAt, h2OsqueryFetched.LastEnrolledAt)
+
+		// the hosts compete for the host entry (all have same row id)
+		require.Equal(t, h1Orbit.ID, h2Orbit.ID)
+		require.Equal(t, h1Orbit.ID, h1Osquery.ID)
+		require.Equal(t, h2Orbit.ID, h2Osquery.ID)
+
+		if fromPlatform == "windows" && toPlatform != "windows" {
+			assert.Nil(t, h2OrbitFetched.MDM.EnrollmentStatus)
+			assert.Nil(t, h2OrbitFetched.MDM.ServerURL)
+		} else {
+			require.NotNil(t, h2OrbitFetched.MDM.EnrollmentStatus)
+			assert.Equal(t, *h1WithMdmFetched.MDM.EnrollmentStatus, *h2OrbitFetched.MDM.EnrollmentStatus)
+			require.NotNil(t, h2OrbitFetched.MDM.ServerURL)
+			assert.Equal(t, *h1WithMdmFetched.MDM.ServerURL, *h2OrbitFetched.MDM.ServerURL)
+		}
+	}
+	for _, fromPlatform := range []string{"ubuntu", "windows", "darwin"} {
+		for _, toPlatform := range []string{"ubuntu", "windows", "darwin"} {
+			fromPlatform := fromPlatform
+			toPlatform := toPlatform
+			t.Run("scenarioE_from_"+fromPlatform+"_to_"+toPlatform, func(t *testing.T) {
+				t.Parallel()
+				scenarioE(fromPlatform, toPlatform)
+			})
+		}
+	}
 }
 
 func testHostsEnrollUpdatesMissingInfo(t *testing.T, ds *Datastore) {