diff --git a/changes/29824-delete-installs-that-has-not-reached-hosts b/changes/29824-delete-installs-that-has-not-reached-hosts
new file mode 100644
index 0000000000..a88ae5c93c
--- /dev/null
+++ b/changes/29824-delete-installs-that-has-not-reached-hosts
@@ -0,0 +1 @@
+* Fix stale pending remove apple declarations, if the host was offline while adding and removing the same declaration.
\ No newline at end of file
diff --git a/server/datastore/mysql/apple_mdm.go b/server/datastore/mysql/apple_mdm.go
index 0ca826d790..dbeffbce6a 100644
--- a/server/datastore/mysql/apple_mdm.go
+++ b/server/datastore/mysql/apple_mdm.go
@@ -643,10 +643,10 @@ func cancelAppleHostInstallsForDeletedMDMDeclarations(ctx context.Context, tx sq
 		host_mdm_apple_declarations
 	WHERE
 		declaration_uuid IN (?) AND
-		status IS NULL AND
+		( status IS NULL OR status IN (?) ) AND
 		operation_type = ?`
 
-	stmt, args, err := sqlx.In(delStmt, declUUIDs, fleet.MDMOperationTypeInstall)
+	stmt, args, err := sqlx.In(delStmt, declUUIDs, []fleet.MDMDeliveryStatus{fleet.MDMDeliveryPending, fleet.MDMDeliveryFailed}, fleet.MDMOperationTypeInstall)
 	if err != nil {
 		return ctxerr.Wrap(ctx, err, "building in statement")
 	}
@@ -5888,6 +5888,8 @@ ON DUPLICATE KEY UPDATE
 		}
 	}
 
+	// TODO: Do we want to take action if an update coming from the host is not found in the current "expected" declarations?
+
 	err := ds.withRetryTxx(ctx, func(tx sqlx.ExtContext) error {
 		if len(args) != 0 {
 			stmt := fmt.Sprintf(updateHostDeclarationsStmt, strings.TrimSuffix(insertVals.String(), ","))
diff --git a/server/datastore/mysql/apple_mdm_test.go b/server/datastore/mysql/apple_mdm_test.go
index ce5d97fccb..3206e3f927 100644
--- a/server/datastore/mysql/apple_mdm_test.go
+++ b/server/datastore/mysql/apple_mdm_test.go
@@ -101,6 +101,7 @@ func TestMDMApple(t *testing.T) {
 		{"SetMDMAppleProfilesWithVariables", testSetMDMAppleProfilesWithVariables},
 		{"GetNanoMDMEnrollmentTimes", testGetNanoMDMEnrollmentTimes},
 		{"GetNanoMDMUserEnrollment", testGetNanoMDMUserEnrollment},
+		{"TestDeleteMDMAppleDeclarationWithPendingInstalls", testDeleteMDMAppleDeclarationWithPendingInstalls},
 	}
 
 	for _, c := range cases {
@@ -5526,6 +5527,45 @@ func testSetOrUpdateMDMAppleDDMDeclaration(t *testing.T, ds *Datastore) {
 	require.Equal(t, d1tm1B.DeclarationUUID, d1tm1.DeclarationUUID)
 }
 
+func testDeleteMDMAppleDeclarationWithPendingInstalls(t *testing.T, ds *Datastore) {
+	ctx := t.Context()
+
+	decl, err := ds.NewMDMAppleDeclaration(ctx, &fleet.MDMAppleDeclaration{
+		Identifier: "decl-1",
+		Name:       "decl-1",
+	})
+	require.NoError(t, err)
+
+	host, err := ds.NewHost(ctx, &fleet.Host{
+		Hostname:      "test-host1-name",
+		OsqueryHostID: ptr.String("1337"),
+		NodeKey:       ptr.String("1337"),
+		UUID:          "test-uuid-1",
+		TeamID:        nil,
+		Platform:      "darwin",
+	})
+	require.NoError(t, err)
+	nanoEnroll(t, ds, host, true)
+
+	_, err = ds.BulkSetPendingMDMHostProfiles(ctx, nil, nil, []string{decl.DeclarationUUID}, nil)
+	require.NoError(t, err)
+
+	// verify the correct state of the declaration for the host
+	profs, err := ds.GetHostMDMAppleProfiles(ctx, host.UUID)
+	require.NoError(t, err)
+	require.Len(t, profs, 1)
+	require.Equal(t, decl.DeclarationUUID, profs[0].ProfileUUID)
+	require.Equal(t, fleet.MDMDeliveryPending, *profs[0].Status)
+	require.Equal(t, fleet.MDMOperationTypeInstall, profs[0].OperationType)
+
+	err = ds.DeleteMDMAppleDeclaration(ctx, decl.DeclarationUUID)
+	require.NoError(t, err)
+
+	profs, err = ds.GetHostMDMAppleProfiles(ctx, host.UUID)
+	require.NoError(t, err)
+	require.Len(t, profs, 0)
+}
+
 func TestMDMAppleProfileVerification(t *testing.T) {
 	ds := CreateMySQLDS(t)
 	ctx := t.Context()
diff --git a/server/service/integration_mdm_ddm_test.go b/server/service/integration_mdm_ddm_test.go
index 44626ede13..a35f87624c 100644
--- a/server/service/integration_mdm_ddm_test.go
+++ b/server/service/integration_mdm_ddm_test.go
@@ -470,7 +470,8 @@ func (s *integrationMDMTestSuite) TestAppleDDMSecretVariables() {
 	_, mdmDevice := createHostThenEnrollMDM(s.ds, s.server.URL, t)
 
 	checkDeclarationItemsResp := func(t *testing.T, r fleet.MDMAppleDDMDeclarationItemsResponse, expectedDeclTok string,
-		expectedDeclsByToken map[string]fleet.MDMAppleDeclaration) {
+		expectedDeclsByToken map[string]fleet.MDMAppleDeclaration,
+	) {
 		require.Equal(t, expectedDeclTok, r.DeclarationsToken)
 		require.NotEmpty(t, r.Declarations.Activations)
 		require.Empty(t, r.Declarations.Assets)
@@ -1065,7 +1066,6 @@ func (s *integrationMDMTestSuite) TestAppleDDMStatusReport() {
 	require.NoError(t, err)
 	assertHostDeclarations(mdmHost.UUID, []*fleet.MDMAppleHostDeclaration{
 		{Identifier: "I1", Status: &fleet.MDMDeliveryVerified, OperationType: fleet.MDMOperationTypeInstall},
-		{Identifier: "I2", Status: &fleet.MDMDeliveryPending, OperationType: fleet.MDMOperationTypeRemove},
 	})
 
 	// host sends a report, declaration I2 is removed from the hosts_* table