diff --git a/app/Http/Controllers/Api/AssetsController.php b/app/Http/Controllers/Api/AssetsController.php
index c672781e6f..dd375d0823 100644
--- a/app/Http/Controllers/Api/AssetsController.php
+++ b/app/Http/Controllers/Api/AssetsController.php
@@ -591,6 +591,11 @@ class AssetsController extends Controller
                         }
                     }
                 }
+                if ($field->element == 'checkbox') {
+                    if(is_array($field_val)) {
+                        $field_val = implode(',', $field_val);
+                    }
+                }
 
 
                 $asset->{$field->db_column} = $field_val;
@@ -659,13 +664,22 @@ class AssetsController extends Controller
             // Update custom fields
             if (($model) && (isset($model->fieldset))) {
                 foreach ($model->fieldset->fields as $field) {
+                    $field_val = $request->input($field->db_column, null);
+
                     if ($request->has($field->db_column)) {
                         if ($field->field_encrypted == '1') {
                             if (Gate::allows('admin')) {
-                                $asset->{$field->db_column} = \Crypt::encrypt($request->input($field->db_column));
+                                $asset->{$field->db_column} = Crypt::encrypt($field_val);
                             }
-                        } else {
-                            $asset->{$field->db_column} = $request->input($field->db_column);
+                        }
+                        if ($field->element == 'checkbox') {
+                            if(is_array($field_val)) {
+                                $field_val = implode(',', $field_val);
+                                $asset->{$field->db_column} = $field_val;
+                            }
+                        }
+                        else {
+                            $asset->{$field->db_column} = $field_val;
                         }
                     }
                 }
diff --git a/app/Http/Controllers/AssetModelsController.php b/app/Http/Controllers/AssetModelsController.php
index 484a2e2f85..8d387f968f 100755
--- a/app/Http/Controllers/AssetModelsController.php
+++ b/app/Http/Controllers/AssetModelsController.php
@@ -7,6 +7,7 @@ use App\Http\Requests\ImageUploadRequest;
 use App\Models\Actionlog;
 use App\Models\Asset;
 use App\Models\AssetModel;
+use App\Models\CustomField;
 use App\Models\User;
 use Illuminate\Support\Facades\Auth;
 use Illuminate\Support\Facades\DB;
@@ -486,11 +487,11 @@ class AssetModelsController extends Controller
      * @param  array      $defaultValues
      * @return void
      */
-    private function assignCustomFieldsDefaultValues(AssetModel $model, array $defaultValues)
+    private function assignCustomFieldsDefaultValues(AssetModel $model, array $defaultValues): bool
     {
         $data = array();
         foreach ($defaultValues as $customFieldId => $defaultValue) {
-            $customField = \App\Models\CustomField::find($customFieldId);
+            $customField = CustomField::find($customFieldId);
 
             $data[$customField->db_column] = $defaultValue;
         }
diff --git a/app/Models/CustomFieldset.php b/app/Models/CustomFieldset.php
index a62f96d631..71be28e8a3 100644
--- a/app/Models/CustomFieldset.php
+++ b/app/Models/CustomFieldset.php
@@ -5,6 +5,8 @@ namespace App\Models;
 use Gate;
 use Illuminate\Database\Eloquent\Factories\HasFactory;
 use Illuminate\Database\Eloquent\Model;
+use Illuminate\Support\Facades\Log;
+use Illuminate\Validation\Rule;
 use Watson\Validating\ValidatingTrait;
 
 class CustomFieldset extends Model
@@ -92,8 +94,19 @@ class CustomFieldset extends Model
 
             array_push($rule, $field->attributes['format']);
             $rules[$field->db_column_name()] = $rule;
-            //add not_array to rules for all fields
-            $rules[$field->db_column_name()][] = 'not_array';
+
+            // add not_array to rules for all fields but checkboxes
+            if ($field->element != 'checkbox') {
+                $rules[$field->db_column_name()][] = 'not_array';
+            }
+
+            if ($field->element == 'checkbox') {
+                $rules[$field->db_column_name()][] = 'checkboxes';
+            }
+
+            if ($field->element == 'radio') {
+                $rules[$field->db_column_name()][] = 'radio_buttons';
+            }
         }
 
         return $rules;
diff --git a/app/Providers/ValidationServiceProvider.php b/app/Providers/ValidationServiceProvider.php
index 50468c8d72..803d540865 100644
--- a/app/Providers/ValidationServiceProvider.php
+++ b/app/Providers/ValidationServiceProvider.php
@@ -2,9 +2,12 @@
 
 namespace App\Providers;
 
+use App\Models\CustomField;
 use App\Models\Department;
 use App\Models\Setting;
 use DB;
+use Illuminate\Support\Facades\Crypt;
+use Illuminate\Support\Facades\Log;
 use Illuminate\Support\ServiceProvider;
 use Illuminate\Validation\Rule;
 use Validator;
@@ -294,6 +297,39 @@ class ValidationServiceProvider extends ServiceProvider
         Validator::extend('not_array', function ($attribute, $value, $parameters, $validator) {
             return !is_array($value);
         });
+
+        // This is only used in Models/CustomFieldset.php - it does automatic validation for checkboxes by making sure
+        // that the submitted values actually exist in the options.
+        Validator::extend('checkboxes', function ($attribute, $value, $parameters, $validator){
+            $field = CustomField::where('db_column', $attribute)->first();
+            $options = $field->formatFieldValuesAsArray();
+
+            if(is_array($value)) {
+                $invalid = array_diff($value, $options);
+                if(count($invalid) > 0) {
+                    return false;
+                }
+            }
+
+            // for legacy, allows users to submit a comma separated string of options
+            elseif(!is_array($value)) {
+                $exploded = array_map('trim', explode(',', $value));
+                $invalid = array_diff($exploded, $options);
+                if(count($invalid) > 0) {
+                    return false;
+                }
+            }
+
+            return true;
+        });
+
+        // Validates that a radio button option exists
+        Validator::extend('radio_buttons', function ($attribute, $value) {
+            $field = CustomField::where('db_column', $attribute)->first();
+            $options = $field->formatFieldValuesAsArray();
+
+            return in_array($value, $options);
+        });
     }
 
     /**
diff --git a/resources/lang/en-US/validation.php b/resources/lang/en-US/validation.php
index 1c6ad8a148..d027a93f86 100644
--- a/resources/lang/en-US/validation.php
+++ b/resources/lang/en-US/validation.php
@@ -105,6 +105,8 @@ return [
     'gte'                  => [
         'numeric'          => 'Value cannot be negative'
     ],
+    'checkboxes'           => ':attribute contains invalid options.',
+    'radio_buttons'        => ':attribute is invalid.',
 
 
     /*
diff --git a/resources/views/custom_fields/fields/edit.blade.php b/resources/views/custom_fields/fields/edit.blade.php
index 504b556faa..e21e9fba48 100644
--- a/resources/views/custom_fields/fields/edit.blade.php
+++ b/resources/views/custom_fields/fields/edit.blade.php
@@ -135,7 +135,7 @@
 
           @if (!$field->id)
               <!-- Encrypted  -->
-              <div class="col-md-9 col-md-offset-3">
+              <div class="col-md-9 col-md-offset-3" id="encryption_section">
                   <label class="form-control">
                       <input type="checkbox" value="1" name="field_encrypted" id="field_encrypted"{{ (Request::old('field_encrypted') || $field->field_encrypted) ? ' checked="checked"' : '' }}>
                       {{ trans('admin/custom_fields/general.encrypt_field') }}
@@ -146,7 +146,6 @@
                       <p><i class="fas fa-exclamation-triangle" aria-hidden="true"></i> {{ trans('admin/custom_fields/general.encrypt_field_help') }}</p>
                   </div>
               </div>
-
           @endif
 
 
@@ -298,11 +297,16 @@
         }).change();
 
         // Only display the field element if the type is not text
+        // and don't display encryption option for checkbox or radio
         $(".field_element").change(function(){
             $(this).find("option:selected").each(function(){
                 if (($(this).attr("value")!="text") && ($(this).attr("value")!="textarea")){
                     $("#field_values_text").show();
+                if ($(this).attr("value") == "checkbox" || $(this).attr("value") == "radio") {
+                    $("#encryption_section").hide();
+                }
                 } else{
+                    $("#encryption_section").show();
                     $("#field_values_text").hide();
                 }
             });