diff --git a/changes/26553-renew-digicert b/changes/26553-renew-digicert
new file mode 100644
index 0000000000..096f02200d
--- /dev/null
+++ b/changes/26553-renew-digicert
@@ -0,0 +1 @@
+Fleet-managed DigiCert certificates will be renewed 30 days before expiry for those valid longer than 30 days or when half the validity period remains for certificates valid 30 days or less. This only applies to certificates that were initially requested after this feature was added. For hosts with DigiCert certificates originally requested prior to this renew feature, manually resending the profile will generate a new certificate which will be automatically renewed before its next expiry.
diff --git a/cmd/fleet/cron.go b/cmd/fleet/cron.go
index 2270a71b04..63db84d291 100644
--- a/cmd/fleet/cron.go
+++ b/cmd/fleet/cron.go
@@ -933,6 +933,9 @@ func newCleanupsAndAggregationSchedule(
 				return service.RenewSCEPCertificates(ctx, logger, ds, config, commander)
 			},
 		),
+		schedule.WithJob("renew_host_mdm_managed_certificates", func(ctx context.Context) error {
+			return ds.RenewMDMManagedCertificates(ctx)
+		}),
 		schedule.WithJob("query_results_cleanup", func(ctx context.Context) error {
 			config, err := ds.AppConfig(ctx)
 			if err != nil {
diff --git a/ee/server/service/digicert/digicert.go b/ee/server/service/digicert/digicert.go
index 991b0950d8..ba68898a31 100644
--- a/ee/server/service/digicert/digicert.go
+++ b/ee/server/service/digicert/digicert.go
@@ -6,6 +6,7 @@ import (
 	"crypto/rsa"
 	"crypto/x509"
 	"crypto/x509/pkix"
+	"encoding/hex"
 	"encoding/pem"
 	"net/http"
 	"net/url"
@@ -66,7 +67,6 @@ func WithLogger(logger kitlog.Logger) Opt {
 }
 
 func (s *Service) VerifyProfileID(ctx context.Context, config fleet.DigiCertIntegration) error {
-
 	client := fleethttp.NewClient(fleethttp.WithTimeout(s.timeout))
 
 	config.URL = strings.TrimRight(config.URL, "/")
@@ -251,6 +251,13 @@ func (s *Service) GetCertificate(ctx context.Context, config fleet.DigiCertInteg
 		return nil, ctxerr.Errorf(ctx, "unexpected DigiCert delivery format: %s", certResp.DeliveryFormat)
 	}
 
+	// Serial number is an up to 20-byte(40 char) hex string
+	_, err = hex.DecodeString(certResp.SerialNumber)
+	if err != nil || certResp.SerialNumber == "" || len(certResp.SerialNumber) > 40 {
+		level.Error(s.logger).Log("msg", "DigiCert certificate returned with invalid serial number", "serial_number", certResp.SerialNumber, "decode_err", err)
+		return nil, ctxerr.Errorf(ctx, "invalid DigiCert serial number: %s", certResp.SerialNumber)
+	}
+
 	if len(certResp.Certificate) == 0 {
 		return nil, ctxerr.Errorf(ctx, "did not receive DigiCert certificate")
 	}
@@ -279,8 +286,10 @@ func (s *Service) GetCertificate(ctx context.Context, config fleet.DigiCertInteg
 	}
 
 	return &fleet.DigiCertCertificate{
-		PfxData:       pkcs12Data,
-		Password:      password,
-		NotValidAfter: cert.NotAfter,
+		PfxData:        pkcs12Data,
+		Password:       password,
+		NotValidBefore: cert.NotBefore,
+		NotValidAfter:  cert.NotAfter,
+		SerialNumber:   certResp.SerialNumber,
 	}, nil
 }
diff --git a/server/datastore/mysql/apple_mdm.go b/server/datastore/mysql/apple_mdm.go
index dde5ff4845..f2b9d2b38f 100644
--- a/server/datastore/mysql/apple_mdm.go
+++ b/server/datastore/mysql/apple_mdm.go
@@ -521,9 +521,11 @@ func (ds *Datastore) GetHostMDMCertificateProfile(ctx context.Context, hostUUID
 		hmap.profile_uuid,
 		hmap.status,
 		hmmc.challenge_retrieved_at,
+		hmmc.not_valid_before,
 		hmmc.not_valid_after,
 		hmmc.type,
-		hmmc.ca_name
+		hmmc.ca_name,
+		hmmc.serial
 	FROM
 		host_mdm_apple_profiles hmap
 	JOIN host_mdm_managed_certificates hmmc
@@ -551,6 +553,65 @@ func (ds *Datastore) CleanUpMDMManagedCertificates(ctx context.Context) error {
 	return nil
 }
 
+// RenewMDMManagedCertificates marks managed certificate profiles for resend when renewal is required
+func (ds *Datastore) RenewMDMManagedCertificates(ctx context.Context) error {
+	// Fetch all MDM Managed digicert certificates that aren't already queued for resend(hmap.status=null) and which
+	// * Have a validity period > 30 days and are expiring in the next 30 days
+	// * Have a validity period <= 30 days and are within half the validity period of expiration
+	// nb: we SELECT not_valid_after and validity_period here so we can use them in the HAVING clause, but
+	// we don't actually need them for the update logic.
+	hostCertsToRenew := []struct {
+		HostUUID       string    `db:"host_uuid"`
+		ProfileUUID    string    `db:"profile_uuid"`
+		NotValidAfter  time.Time `db:"not_valid_after"`
+		ValidityPeriod int       `db:"validity_period"`
+	}{}
+	err := sqlx.SelectContext(ctx, ds.reader(ctx), &hostCertsToRenew, `
+	SELECT
+		hmmc.host_uuid, 
+		hmmc.profile_uuid, 
+		hmmc.not_valid_after, 
+		DATEDIFF(hmmc.not_valid_after, hmmc.not_valid_before) AS validity_period
+	FROM 
+		host_mdm_managed_certificates hmmc
+	INNER JOIN 
+		host_mdm_apple_profiles hmap 
+		ON hmmc.host_uuid = hmap.host_uuid AND hmmc.profile_uuid = hmap.profile_uuid
+	WHERE 
+		hmmc.type = ? AND hmap.status IS NOT NULL
+	HAVING
+		validity_period IS NOT NULL AND
+		((validity_period > 30 AND not_valid_after < DATE_ADD(NOW(), INTERVAL 30 DAY)) OR
+		(validity_period <= 30 AND not_valid_after < DATE_ADD(NOW(), INTERVAL validity_period/2 DAY)))
+	LIMIT 1000`, fleet.CAConfigDigiCert)
+	if err != nil {
+		return ctxerr.Wrap(ctx, err, "retrieving mdm managed certificates to renew")
+	}
+	if len(hostCertsToRenew) == 0 {
+		level.Debug(ds.logger).Log("msg", "No digicert certificates to renew")
+		return nil
+	}
+
+	// This will trigger a resend next time profiles are checked
+	updateQuery := `UPDATE host_mdm_apple_profiles SET status = NULL WHERE `
+	hostProfileClause := ``
+	values := []interface{}{}
+	for _, hostCertToRenew := range hostCertsToRenew {
+		hostProfileClause += `(host_uuid = ? AND profile_uuid = ?) OR `
+		values = append(values, hostCertToRenew.HostUUID, hostCertToRenew.ProfileUUID)
+	}
+
+	level.Debug(ds.logger).Log("msg", "Renewing MDM managed digicert certificates", "len(hostCertsToRenew)", len(hostCertsToRenew))
+	err = ds.withRetryTxx(ctx, func(tx sqlx.ExtContext) error {
+		_, err := tx.ExecContext(ctx, updateQuery+strings.TrimSuffix(hostProfileClause, " OR "), values...)
+		if err != nil {
+			return ctxerr.Wrap(ctx, err, "updating mdm managed certificates to renew")
+		}
+		return nil
+	})
+	return err
+}
+
 func (ds *Datastore) NewMDMAppleEnrollmentProfile(
 	ctx context.Context,
 	payload fleet.MDMAppleEnrollmentProfilePayload,
@@ -5883,16 +5944,20 @@ func (ds *Datastore) BulkUpsertMDMManagedCertificates(ctx context.Context, paylo
               host_uuid,
               profile_uuid,
               challenge_retrieved_at,
+			  not_valid_before,
 	          not_valid_after,
 			  type,
-			  ca_name
+			  ca_name,
+			  serial
             )
             VALUES %s
             ON DUPLICATE KEY UPDATE
               challenge_retrieved_at = VALUES(challenge_retrieved_at),
+			  not_valid_before = VALUES(not_valid_before),
 			  not_valid_after = VALUES(not_valid_after),
 			  type = VALUES(type),
-			  ca_name = VALUES(ca_name)`,
+			  ca_name = VALUES(ca_name),
+			  serial = VALUES(serial)`,
 			strings.TrimSuffix(valuePart, ","),
 		)
 
@@ -5901,8 +5966,8 @@ func (ds *Datastore) BulkUpsertMDMManagedCertificates(ctx context.Context, paylo
 	}
 
 	generateValueArgs := func(p *fleet.MDMBulkUpsertManagedCertificatePayload) (string, []any) {
-		valuePart := "(?, ?, ?, ?, ?, ?),"
-		args := []any{p.HostUUID, p.ProfileUUID, p.ChallengeRetrievedAt, p.NotValidAfter, p.Type, p.CAName}
+		valuePart := "(?, ?, ?, ?, ?, ?, ?, ?),"
+		args := []any{p.HostUUID, p.ProfileUUID, p.ChallengeRetrievedAt, p.NotValidBefore, p.NotValidAfter, p.Type, p.CAName, p.Serial}
 		return valuePart, args
 	}
 
diff --git a/server/datastore/mysql/apple_mdm_test.go b/server/datastore/mysql/apple_mdm_test.go
index 8ae089b909..243c3156ec 100644
--- a/server/datastore/mysql/apple_mdm_test.go
+++ b/server/datastore/mysql/apple_mdm_test.go
@@ -90,7 +90,8 @@ func TestMDMApple(t *testing.T) {
 		{"TestMDMGetABMTokenOrgNamesAssociatedWithTeam", testMDMGetABMTokenOrgNamesAssociatedWithTeam},
 		{"HostMDMCommands", testHostMDMCommands},
 		{"IngestMDMAppleDeviceFromOTAEnrollment", testIngestMDMAppleDeviceFromOTAEnrollment},
-		{"MDMManagedCertificates", testMDMManagedCertificates},
+		{"MDMManagedSCEPCertificates", testMDMManagedSCEPCertificates},
+		{"MDMManagedDigicertCertificates", testMDMManagedDigicertCertificates},
 		{"AppleMDMSetBatchAsyncLastSeenAt", testAppleMDMSetBatchAsyncLastSeenAt},
 		{"TestMDMAppleProfileLabels", testMDMAppleProfileLabels},
 		{"AggregateMacOSSettingsAllPlatforms", testAggregateMacOSSettingsAllPlatforms},
@@ -608,7 +609,6 @@ func testHostDetailsMDMProfiles(t *testing.T, ds *Datastore) {
 	require.NoError(t, err)
 	require.Len(t, gotProfs, 1)
 	assert.Equal(t, &fleet.MDMDeliveryVerifying, gotProfs[0].Status)
-
 }
 
 func TestIngestMDMAppleDevicesFromDEPSync(t *testing.T) {
@@ -2676,7 +2676,8 @@ func testDeleteMDMAppleProfilesForHost(t *testing.T, ds *Datastore) {
 }
 
 func createDiskEncryptionRecord(ctx context.Context, ds *Datastore, t *testing.T, host *fleet.Host, key string, decryptable bool,
-	threshold time.Time) {
+	threshold time.Time,
+) {
 	err := ds.SetOrUpdateHostDiskEncryptionKey(ctx, host, key, "", nil)
 	require.NoError(t, err)
 	err = ds.SetHostsDiskEncryptionKeyStatus(ctx, []uint{host.ID}, decryptable, threshold)
@@ -7190,7 +7191,7 @@ func TestGetMDMAppleOSUpdatesSettingsByHostSerial(t *testing.T) {
 	require.ErrorIs(t, err, sql.ErrNoRows)
 }
 
-func testMDMManagedCertificates(t *testing.T, ds *Datastore) {
+func testMDMManagedSCEPCertificates(t *testing.T, ds *Datastore) {
 	ctx := context.Background()
 	initialCP := storeDummyConfigProfileForTest(t, ds)
 	host, err := ds.NewHost(ctx, &fleet.Host{
@@ -7231,12 +7232,14 @@ func testMDMManagedCertificates(t *testing.T, ds *Datastore) {
 	assert.Nil(t, profile)
 
 	challengeRetrievedAt := time.Now().Add(-time.Hour).UTC().Round(time.Microsecond)
+	notValidBefore := time.Now().UTC().Round(time.Microsecond)
 	notValidAfter := time.Now().Add(24 * time.Hour).UTC().Round(time.Microsecond)
 	err = ds.BulkUpsertMDMManagedCertificates(ctx, []*fleet.MDMBulkUpsertManagedCertificatePayload{
 		{
 			HostUUID:             host.UUID,
 			ProfileUUID:          initialCP.ProfileUUID,
 			ChallengeRetrievedAt: &challengeRetrievedAt,
+			NotValidBefore:       &notValidBefore,
 			NotValidAfter:        &notValidAfter,
 			Type:                 fleet.CAConfigCustomSCEPProxy,
 			CAName:               "test-ca",
@@ -7252,10 +7255,20 @@ func testMDMManagedCertificates(t *testing.T, ds *Datastore) {
 	assert.Equal(t, initialCP.ProfileUUID, profile.ProfileUUID)
 	require.NotNil(t, profile.ChallengeRetrievedAt)
 	assert.Equal(t, &challengeRetrievedAt, profile.ChallengeRetrievedAt)
+	assert.Equal(t, &notValidBefore, profile.NotValidBefore)
 	assert.Equal(t, &notValidAfter, profile.NotValidAfter)
 	assert.Equal(t, fleet.CAConfigCustomSCEPProxy, profile.Type)
+	assert.Nil(t, profile.Serial)
 	assert.Equal(t, "test-ca", profile.CAName)
 
+	// Renew should do nothing for SCEP
+	err = ds.RenewMDMManagedCertificates(ctx)
+	require.NoError(t, err)
+	profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+	require.NoError(t, err)
+	require.NotNil(t, profile.Status)
+	assert.Equal(t, fleet.MDMDeliveryPending, *profile.Status)
+
 	// Cleanup should do nothing
 	err = ds.CleanUpMDMManagedCertificates(ctx)
 	require.NoError(t, err)
@@ -7290,6 +7303,232 @@ func testMDMManagedCertificates(t *testing.T, ds *Datastore) {
 	require.ErrorIs(t, err, sql.ErrNoRows)
 }
 
+func testMDMManagedDigicertCertificates(t *testing.T, ds *Datastore) {
+	ctx := context.Background()
+	initialCP := storeDummyConfigProfileForTest(t, ds)
+	host, err := ds.NewHost(ctx, &fleet.Host{
+		DetailUpdatedAt: time.Now(),
+		LabelUpdatedAt:  time.Now(),
+		PolicyUpdatedAt: time.Now(),
+		SeenTime:        time.Now(),
+		OsqueryHostID:   ptr.String("host0-osquery-id"),
+		NodeKey:         ptr.String("host0-node-key"),
+		UUID:            "host0-test-mdm-profiles",
+		Hostname:        "hostname0",
+	})
+	require.NoError(t, err)
+
+	// Host and profile are not linked
+	profile, err := ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+	require.NoError(t, err)
+	assert.Nil(t, profile)
+
+	err = ds.BulkUpsertMDMAppleHostProfiles(ctx, []*fleet.MDMAppleBulkUpsertHostProfilePayload{
+		{
+			ProfileUUID:       initialCP.ProfileUUID,
+			ProfileIdentifier: initialCP.Identifier,
+			ProfileName:       initialCP.Name,
+			HostUUID:          host.UUID,
+			Status:            &fleet.MDMDeliveryVerified,
+			OperationType:     fleet.MDMOperationTypeInstall,
+			CommandUUID:       "command-uuid",
+			Checksum:          []byte("checksum"),
+		},
+	},
+	)
+	require.NoError(t, err)
+
+	// Host and profile do not have certificate metadata
+	profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+	require.NoError(t, err)
+	assert.Nil(t, profile)
+
+	notValidBefore := time.Now().UTC().Round(time.Microsecond)
+	notValidAfter := time.Now().Add(29 * 24 * time.Hour).UTC().Round(time.Microsecond)
+	serial := "3ABADCAFEF684D6348F5EC95AEFF468F237A9D7E"
+	err = ds.BulkUpsertMDMManagedCertificates(ctx, []*fleet.MDMBulkUpsertManagedCertificatePayload{
+		{
+			HostUUID:             host.UUID,
+			ProfileUUID:          initialCP.ProfileUUID,
+			ChallengeRetrievedAt: nil,
+			NotValidBefore:       &notValidBefore,
+			NotValidAfter:        &notValidAfter,
+			Type:                 fleet.CAConfigDigiCert,
+			CAName:               "test-ca",
+			Serial:               &serial,
+		},
+	})
+	require.NoError(t, err)
+
+	// Check that the managed certificate was inserted correctly
+	profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+	require.NoError(t, err)
+	require.NotNil(t, profile)
+	assert.Equal(t, host.UUID, profile.HostUUID)
+	assert.Equal(t, initialCP.ProfileUUID, profile.ProfileUUID)
+	assert.Nil(t, profile.ChallengeRetrievedAt)
+	assert.Equal(t, &notValidBefore, profile.NotValidBefore)
+	assert.Equal(t, &notValidAfter, profile.NotValidAfter)
+	assert.Equal(t, fleet.CAConfigDigiCert, profile.Type)
+	require.NotNil(t, profile.Serial)
+	assert.Equal(t, serial, *profile.Serial)
+	assert.Equal(t, "test-ca", profile.CAName)
+
+	// Renew should not do anything yet so the MDM delivery status should stay "verified"
+	err = ds.RenewMDMManagedCertificates(ctx)
+	require.NoError(t, err)
+	profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+	require.NoError(t, err)
+	require.NotNil(t, profile.Status)
+	assert.Equal(t, fleet.MDMDeliveryVerified, *profile.Status)
+
+	t.Run("Renew scenario 1 - validity window > 30 days", func(t *testing.T) {
+		// Set not_valid_before to 31 days in the past the validity window becomes 60 days, of which there are
+		// 29 left which should trigger the first renewal scenario(window > 30 days, renew when < 30
+		// days left)
+		notValidBefore := time.Now().Add(-31 * 24 * time.Hour).UTC().Round(time.Microsecond)
+		err = ds.BulkUpsertMDMManagedCertificates(ctx, []*fleet.MDMBulkUpsertManagedCertificatePayload{
+			{
+				HostUUID:             host.UUID,
+				ProfileUUID:          initialCP.ProfileUUID,
+				ChallengeRetrievedAt: nil,
+				NotValidBefore:       &notValidBefore,
+				NotValidAfter:        &notValidAfter,
+				Type:                 fleet.CAConfigDigiCert,
+				CAName:               "test-ca",
+				Serial:               &serial,
+			},
+		})
+		ExecAdhocSQL(t, ds, func(q sqlx.ExtContext) error {
+			_, err := q.ExecContext(ctx, `
+			UPDATE host_mdm_apple_profiles SET status = ? WHERE host_uuid = ? AND profile_uuid = ?
+		`, fleet.MDMDeliveryVerified, host.UUID, initialCP.ProfileUUID)
+			if err != nil {
+				return err
+			}
+			return nil
+		})
+
+		// Verify the policy is not currently marked for resend and that the upsert executed correctly
+		profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+		require.NoError(t, err)
+		require.NotNil(t, profile.Status)
+		assert.Equal(t, fleet.MDMDeliveryVerified, *profile.Status)
+
+		assert.Equal(t, host.UUID, profile.HostUUID)
+		assert.Equal(t, initialCP.ProfileUUID, profile.ProfileUUID)
+		assert.Nil(t, profile.ChallengeRetrievedAt)
+		assert.Equal(t, &notValidBefore, profile.NotValidBefore)
+		assert.Equal(t, &notValidAfter, profile.NotValidAfter)
+		assert.Equal(t, fleet.CAConfigDigiCert, profile.Type)
+		require.NotNil(t, profile.Serial)
+		assert.Equal(t, serial, *profile.Serial)
+		assert.Equal(t, "test-ca", profile.CAName)
+
+		// Renew should set the MDM delivery status to "null" so the profile gets resent and the certificate renewed
+		err = ds.RenewMDMManagedCertificates(ctx)
+		require.NoError(t, err)
+		profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+		require.NoError(t, err)
+		require.Nil(t, profile.Status)
+
+		// Cleanup should do nothing
+		err = ds.CleanUpMDMManagedCertificates(ctx)
+		require.NoError(t, err)
+		profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+		require.NoError(t, err)
+		require.NotNil(t, profile)
+	})
+
+	t.Run("Renew scenario 2 - validity window < 30 days", func(t *testing.T) {
+		// Set not_valid_before to 15 days in the past and not_valid_after to 14 days in the future so the
+		// validity window becomes 29 days, of which there are 14 left which should trigger the second
+		// renewal scenario(window < 30 days, renew when there is half that time left)
+		notValidBefore := time.Now().Add(-15 * 24 * time.Hour).UTC().Round(time.Microsecond)
+		notValidAfter := time.Now().Add(14 * 24 * time.Hour).UTC().Round(time.Microsecond)
+		err = ds.BulkUpsertMDMManagedCertificates(ctx, []*fleet.MDMBulkUpsertManagedCertificatePayload{
+			{
+				HostUUID:             host.UUID,
+				ProfileUUID:          initialCP.ProfileUUID,
+				ChallengeRetrievedAt: nil,
+				NotValidBefore:       &notValidBefore,
+				NotValidAfter:        &notValidAfter,
+				Type:                 fleet.CAConfigDigiCert,
+				CAName:               "test-ca",
+				Serial:               &serial,
+			},
+		})
+		require.NoError(t, err)
+
+		ExecAdhocSQL(t, ds, func(q sqlx.ExtContext) error {
+			_, err := q.ExecContext(ctx, `
+		UPDATE host_mdm_apple_profiles SET status = ? WHERE host_uuid = ? AND profile_uuid = ?
+	`, fleet.MDMDeliveryVerified, host.UUID, initialCP.ProfileUUID)
+			if err != nil {
+				return err
+			}
+			return nil
+		})
+		require.NoError(t, err)
+
+		// Verify the policy is not currently marked for resend and that the upsert executed correctly
+		profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+		require.NoError(t, err)
+		require.NotNil(t, profile.Status)
+		assert.Equal(t, fleet.MDMDeliveryVerified, *profile.Status)
+
+		assert.Equal(t, host.UUID, profile.HostUUID)
+		assert.Equal(t, initialCP.ProfileUUID, profile.ProfileUUID)
+		assert.Nil(t, profile.ChallengeRetrievedAt)
+		assert.Equal(t, &notValidBefore, profile.NotValidBefore)
+		assert.Equal(t, &notValidAfter, profile.NotValidAfter)
+		assert.Equal(t, fleet.CAConfigDigiCert, profile.Type)
+		require.NotNil(t, profile.Serial)
+		assert.Equal(t, serial, *profile.Serial)
+		assert.Equal(t, "test-ca", profile.CAName)
+
+		// Renew should set the MDM delivery status to "null" so the profile gets resent and the certificate renewed
+		err = ds.RenewMDMManagedCertificates(ctx)
+		require.NoError(t, err)
+		profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+		require.NoError(t, err)
+		require.Nil(t, profile.Status)
+
+		// Cleanup should do nothing
+		err = ds.CleanUpMDMManagedCertificates(ctx)
+		require.NoError(t, err)
+		profile, err = ds.GetHostMDMCertificateProfile(ctx, host.UUID, initialCP.ProfileUUID, "test-ca")
+		require.NoError(t, err)
+		require.NotNil(t, profile)
+	})
+
+	badProfileUUID := uuid.NewString()
+	ExecAdhocSQL(t, ds, func(q sqlx.ExtContext) error {
+		_, err := q.ExecContext(ctx, `
+			INSERT INTO host_mdm_managed_certificates (host_uuid, profile_uuid) VALUES (?, ?)
+		`, host.UUID, badProfileUUID)
+		if err != nil {
+			return err
+		}
+		return nil
+	})
+	var uid string
+	ExecAdhocSQL(t, ds, func(q sqlx.ExtContext) error {
+		return sqlx.GetContext(ctx, q, &uid, `SELECT profile_uuid FROM host_mdm_managed_certificates WHERE profile_uuid = ?`,
+			badProfileUUID)
+	})
+	require.Equal(t, badProfileUUID, uid)
+
+	// Cleanup should delete the above orphaned record
+	err = ds.CleanUpMDMManagedCertificates(ctx)
+	require.NoError(t, err)
+	err = ExecAdhocSQLWithError(ds, func(q sqlx.ExtContext) error {
+		return sqlx.GetContext(ctx, q, &uid, `SELECT profile_uuid FROM host_mdm_managed_certificates WHERE profile_uuid = ?`,
+			badProfileUUID)
+	})
+	require.ErrorIs(t, err, sql.ErrNoRows)
+}
+
 func testAppleMDMSetBatchAsyncLastSeenAt(t *testing.T, ds *Datastore) {
 	ctx := context.Background()
 
diff --git a/server/datastore/mysql/migrations/tables/20250421085116_AddSerialAndNotBeforeToHostMDMManagedCertificates.go b/server/datastore/mysql/migrations/tables/20250421085116_AddSerialAndNotBeforeToHostMDMManagedCertificates.go
new file mode 100644
index 0000000000..1b3b8b8151
--- /dev/null
+++ b/server/datastore/mysql/migrations/tables/20250421085116_AddSerialAndNotBeforeToHostMDMManagedCertificates.go
@@ -0,0 +1,29 @@
+package tables
+
+import (
+	"database/sql"
+	"fmt"
+)
+
+func init() {
+	MigrationClient.AddMigration(Up_20250421085116, Down_20250421085116)
+}
+
+func Up_20250421085116(tx *sql.Tx) error {
+	if columnsExists(tx, "host_mdm_managed_certificates", "serial", "not_valid_before") {
+		return nil
+	}
+	_, err := tx.Exec(`
+	ALTER TABLE host_mdm_managed_certificates
+	ADD COLUMN serial varchar(40) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci,
+	ADD COLUMN not_valid_before datetime(6) NULL
+	`)
+	if err != nil {
+		return fmt.Errorf("failed to add serial columns to host_mdm_managed_certificates table: %s", err)
+	}
+	return nil
+}
+
+func Down_20250421085116(tx *sql.Tx) error {
+	return nil
+}
diff --git a/server/datastore/mysql/schema.sql b/server/datastore/mysql/schema.sql
index da315c317c..d1a7f200d8 100644
--- a/server/datastore/mysql/schema.sql
+++ b/server/datastore/mysql/schema.sql
@@ -556,6 +556,8 @@ CREATE TABLE `host_mdm_managed_certificates` (
   `created_at` timestamp(6) NOT NULL DEFAULT CURRENT_TIMESTAMP(6),
   `updated_at` timestamp(6) NOT NULL DEFAULT CURRENT_TIMESTAMP(6) ON UPDATE CURRENT_TIMESTAMP(6),
   `not_valid_after` datetime(6) DEFAULT NULL,
+  `serial` varchar(40) CHARACTER SET utf8mb4 COLLATE utf8mb4_unicode_ci DEFAULT NULL,
+  `not_valid_before` datetime(6) DEFAULT NULL,
   PRIMARY KEY (`host_uuid`,`profile_uuid`,`ca_name`)
 ) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
@@ -1220,9 +1222,9 @@ CREATE TABLE `migration_status_tables` (
   `is_applied` tinyint(1) NOT NULL,
   `tstamp` timestamp NULL DEFAULT CURRENT_TIMESTAMP,
   PRIMARY KEY (`id`)
-) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB AUTO_INCREMENT=376 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
+) /*!50100 TABLESPACE `innodb_system` */ ENGINE=InnoDB AUTO_INCREMENT=377 DEFAULT CHARSET=utf8mb4 COLLATE=utf8mb4_unicode_ci;
 /*!40101 SET character_set_client = @saved_cs_client */;
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 /*!40101 SET @saved_cs_client     = @@character_set_client */;
 /*!50503 SET character_set_client = utf8mb4 */;
 CREATE TABLE `mobile_device_management_solutions` (
diff --git a/server/fleet/apple_mdm.go b/server/fleet/apple_mdm.go
index 0a60b47e25..e0630b5440 100644
--- a/server/fleet/apple_mdm.go
+++ b/server/fleet/apple_mdm.go
@@ -292,9 +292,11 @@ type HostMDMCertificateProfile struct {
 	ProfileUUID          string             `db:"profile_uuid"`
 	Status               *MDMDeliveryStatus `db:"status"`
 	ChallengeRetrievedAt *time.Time         `db:"challenge_retrieved_at"`
+	NotValidBefore       *time.Time         `db:"not_valid_before"`
 	NotValidAfter        *time.Time         `db:"not_valid_after"`
 	Type                 CAConfigAssetType  `db:"type"`
 	CAName               string             `db:"ca_name"`
+	Serial               *string            `db:"serial"`
 }
 
 type HostMDMProfileDetail string
@@ -976,9 +978,11 @@ type MDMBulkUpsertManagedCertificatePayload struct {
 	ProfileUUID          string
 	HostUUID             string
 	ChallengeRetrievedAt *time.Time
+	NotValidBefore       *time.Time
 	NotValidAfter        *time.Time
 	Type                 CAConfigAssetType
 	CAName               string
+	Serial               *string
 }
 
 // MDMAppleEnrolledDeviceInfo represents the information of a device enrolled
diff --git a/server/fleet/datastore.go b/server/fleet/datastore.go
index fc1a86d1c7..055f570986 100644
--- a/server/fleet/datastore.go
+++ b/server/fleet/datastore.go
@@ -1993,6 +1993,9 @@ type Datastore interface {
 	// CleanUpMDMManagedCertificates removes all managed certificates that are not associated with any host+profile.
 	CleanUpMDMManagedCertificates(ctx context.Context) error
 
+	// RenewMDMManagedCertificates marks managed certificate profiles for resend when renewal is required
+	RenewMDMManagedCertificates(ctx context.Context) error
+
 	// /////////////////////////////////////////////////////////////////////////////
 	// Secret variables
 
diff --git a/server/fleet/digicert.go b/server/fleet/digicert.go
index 70f0d7a20b..901496f11e 100644
--- a/server/fleet/digicert.go
+++ b/server/fleet/digicert.go
@@ -6,9 +6,11 @@ import (
 )
 
 type DigiCertCertificate struct {
-	PfxData       []byte
-	Password      string
-	NotValidAfter time.Time
+	PfxData        []byte
+	Password       string
+	NotValidBefore time.Time
+	NotValidAfter  time.Time
+	SerialNumber   string
 }
 
 type DigiCertService interface {
diff --git a/server/mock/datastore_mock.go b/server/mock/datastore_mock.go
index d3147ed475..3aba3cfa19 100644
--- a/server/mock/datastore_mock.go
+++ b/server/mock/datastore_mock.go
@@ -1252,6 +1252,8 @@ type GetHostMDMCertificateProfileFunc func(ctx context.Context, hostUUID string,
 
 type CleanUpMDMManagedCertificatesFunc func(ctx context.Context) error
 
+type RenewMDMManagedCertificatesFunc func(ctx context.Context) error
+
 type UpsertSecretVariablesFunc func(ctx context.Context, secretVariables []fleet.SecretVariable) error
 
 type GetSecretVariablesFunc func(ctx context.Context, names []string) ([]fleet.SecretVariable, error)
@@ -3168,6 +3170,9 @@ type DataStore struct {
 	CleanUpMDMManagedCertificatesFunc        CleanUpMDMManagedCertificatesFunc
 	CleanUpMDMManagedCertificatesFuncInvoked bool
 
+	RenewMDMManagedCertificatesFunc        RenewMDMManagedCertificatesFunc
+	RenewMDMManagedCertificatesFuncInvoked bool
+
 	UpsertSecretVariablesFunc        UpsertSecretVariablesFunc
 	UpsertSecretVariablesFuncInvoked bool
 
@@ -7581,6 +7586,13 @@ func (s *DataStore) CleanUpMDMManagedCertificates(ctx context.Context) error {
 	return s.CleanUpMDMManagedCertificatesFunc(ctx)
 }
 
+func (s *DataStore) RenewMDMManagedCertificates(ctx context.Context) error {
+	s.mu.Lock()
+	s.RenewMDMManagedCertificatesFuncInvoked = true
+	s.mu.Unlock()
+	return s.RenewMDMManagedCertificatesFunc(ctx)
+}
+
 func (s *DataStore) UpsertSecretVariables(ctx context.Context, secretVariables []fleet.SecretVariable) error {
 	s.mu.Lock()
 	s.UpsertSecretVariablesFuncInvoked = true
diff --git a/server/service/apple_mdm.go b/server/service/apple_mdm.go
index ff49519d6f..0871401a24 100644
--- a/server/service/apple_mdm.go
+++ b/server/service/apple_mdm.go
@@ -4383,11 +4383,13 @@ func preprocessProfileContents(
 						return ctxerr.Wrap(ctx, err, "replacing Fleet variable for DigiCert password")
 					}
 					managedCertificatePayloads = append(managedCertificatePayloads, &fleet.MDMBulkUpsertManagedCertificatePayload{
-						HostUUID:      hostUUID,
-						ProfileUUID:   profUUID,
-						NotValidAfter: &cert.NotValidAfter,
-						Type:          fleet.CAConfigDigiCert,
-						CAName:        caName,
+						HostUUID:       hostUUID,
+						ProfileUUID:    profUUID,
+						NotValidBefore: &cert.NotValidBefore,
+						NotValidAfter:  &cert.NotValidAfter,
+						Type:           fleet.CAConfigDigiCert,
+						CAName:         caName,
+						Serial:         &cert.SerialNumber,
 					})
 
 				default: