diff --git a/docs/releases/2.5.rst b/docs/releases/2.5.rst
index 4d93c6f09e..0084d7e73e 100644
--- a/docs/releases/2.5.rst
+++ b/docs/releases/2.5.rst
@@ -44,7 +44,14 @@ Other Changes
   its own separate $HOME directory. Additionally give every libreoffice
   its own UserInstallation file in the $HOME directory. Works around
   Libre Office issue: https://bugs.documentfoundation.org/show_bug.cgi?id=37531
-  Solves or affects GitLab issues #393 #258 #198 #175 
+  Solves or affects GitLab issues #393 #258 #198 #175
+- Document type-metadata type relationship. Add new UI method to switch between
+  required metadata and optional metadata for a document type. This new
+  method does not forces users to remove a metadata type before making the
+  switch and thus avoid deletion of existing metadata entries. GitLab issue #337.
+- It is now possible to change the relationship between metadata types and
+  document types from either the metadata type list or document type list.
+  GitLab issue #373.
 
 
 Removals
@@ -103,5 +110,7 @@ Bugs fixed or issues closed
 * `GitHub issue #255 <https://github.com/mayan-edms/mayan-edms/issues/255>`_ Uploading a local file via api
 * `GitLab issue #215 <https://gitlab.com/mayan-edms/mayan-edms/issues/215>`_ Download text contents
 * `GitLab issue #286 <https://gitlab.com/mayan-edms/mayan-edms/issues/286>`_ User configurable mailer
+* `GitLab issue #337 <https://gitlab.com/mayan-edms/mayan-edms/issues/337>`_ Better way to switch Optional to Required Metadata
+* `GitLab issue #373 <https://gitlab.com/mayan-edms/mayan-edms/issues/373>`_ (feature request) Allow selecting document types for metadata
 
 .. _PyPI: https://pypi.python.org/pypi/mayan-edms/
diff --git a/mayan/apps/appearance/templates/appearance/generic_form_instance.html b/mayan/apps/appearance/templates/appearance/generic_form_instance.html
index a65b594acd..ca3b586a82 100644
--- a/mayan/apps/appearance/templates/appearance/generic_form_instance.html
+++ b/mayan/apps/appearance/templates/appearance/generic_form_instance.html
@@ -22,7 +22,17 @@
     {% for field in form.visible_fields %}
         <td title="{% if field.errors %}{% for error in field.errors %}{{ error }}{% if not forloop.last %} | {% endif %}{% endfor %}{% else %}{{ field.help_text }}{% endif %}">
             {% if field.errors %}<div class="has-error">{% endif %}
-              {% render_field field class+="form-control" %}
+                {% if field|widget_type == 'radioselect' %}
+                    <div class="btn-group" data-toggle="buttons">
+                        {% for option in field %}
+                            <label class="btn btn-default {% if field.value == option.choice_value %}active{% endif %}" for="{{ option.attrs.id }}">
+                                <input type="radio" name="{{ option.name }}" id="{{ option.attrs.id }}" value="{{ option.choice_value }}" {% if field.value == option.choice_value %}checked{% endif %}> {{ option.choice_label }}
+                            </label>
+                        {% endfor %}
+                    </div>
+                {% else %}
+                    {% render_field field class+="form-control" %}
+                {% endif %}
             {% if field.errors %}</div>{% endif %}
         </td>
     {% endfor %}
@@ -38,7 +48,6 @@
                 {% if field|widget_type != 'checkboxinput' and not field.field.widget.attrs.hidden %}
                     {% if not hide_labels %}{{ field.label_tag }}{% if field.field.required and not read_only %} ({% trans 'required' %}){% endif %}{% endif %}
                 {% endif %}
-
                 {% if field|widget_type == 'checkboxinput' %}
                     <div class="checkbox">
                         <label>
diff --git a/mayan/apps/metadata/apps.py b/mayan/apps/metadata/apps.py
index 8540f06833..20a24c0367 100644
--- a/mayan/apps/metadata/apps.py
+++ b/mayan/apps/metadata/apps.py
@@ -32,9 +32,8 @@ from .links import (
     link_metadata_add, link_metadata_edit, link_metadata_multiple_add,
     link_metadata_multiple_edit, link_metadata_multiple_remove,
     link_metadata_remove, link_metadata_view,
-    link_setup_document_type_metadata,
-    link_setup_document_type_metadata_required,
-    link_setup_metadata_type_create, link_setup_metadata_type_delete,
+    link_setup_document_type_metadata_types, link_setup_metadata_type_create,
+    link_setup_metadata_type_delete, link_setup_metadata_type_document_types,
     link_setup_metadata_type_edit, link_setup_metadata_type_list,
 )
 from .permissions import (
@@ -206,13 +205,13 @@ class MetadataApp(MayanAppConfig):
         )
         menu_object.bind_links(
             links=(
-                link_setup_document_type_metadata,
-                link_setup_document_type_metadata_required
+                link_setup_document_type_metadata_types,
             ), sources=(DocumentType,)
         )
         menu_object.bind_links(
             links=(
                 link_setup_metadata_type_edit,
+                link_setup_metadata_type_document_types,
                 link_setup_metadata_type_delete
             ), sources=(MetadataType,)
         )
diff --git a/mayan/apps/metadata/forms.py b/mayan/apps/metadata/forms.py
index 568e31e62a..a08024f9f5 100644
--- a/mayan/apps/metadata/forms.py
+++ b/mayan/apps/metadata/forms.py
@@ -170,3 +170,70 @@ class DocumentMetadataRemoveForm(DocumentMetadataForm):
 DocumentMetadataRemoveFormSet = formset_factory(
     DocumentMetadataRemoveForm, extra=0
 )
+
+
+class DocumentTypeMetadataTypeRelationshipForm(forms.Form):
+    label = forms.CharField(
+        label=_('Label'), required=False,
+        widget=forms.TextInput(attrs={'readonly': 'readonly'})
+    )
+    relationship = forms.ChoiceField(
+        label=_('Relationship'),
+        widget=forms.RadioSelect(), choices=(
+            ('none', _('None')),
+            ('optional', _('Optional')),
+            ('required', _('Required')),
+        )
+    )
+
+    def __init__(self, *args, **kwargs):
+        super(DocumentTypeMetadataTypeRelationshipForm, self).__init__(
+            *args, **kwargs
+        )
+        if self.initial['main_model'] == 'metadata_type':
+            self.fields['label'].initial = self.initial['document_type'].label
+        else:
+            self.fields['label'].initial = self.initial['metadata_type'].label
+
+        relationship = self.initial['document_type'].metadata.filter(
+            metadata_type=self.initial['metadata_type']
+        )
+        if relationship.exists():
+            if relationship.get().required:
+                self.fields['relationship'].initial = 'required'
+            else:
+                self.fields['relationship'].initial = 'optional'
+        else:
+            self.fields['relationship'].initial = 'none'
+
+    def save(self):
+        relationship = self.initial['document_type'].metadata.filter(
+            metadata_type=self.initial['metadata_type']
+        )
+        if self.cleaned_data['relationship'] == 'none':
+            relationship.delete()
+        elif self.cleaned_data['relationship'] == 'optional':
+            if relationship.exists():
+                instance = relationship.get()
+                instance.required = False
+                instance.save()
+            else:
+                relationship.create(
+                    document_type=self.initial['document_type'],
+                    metadata_type=self.initial['metadata_type']
+                )
+        elif self.cleaned_data['relationship'] == 'required':
+            if relationship.exists():
+                instance = relationship.get()
+                instance.required = True
+                instance.save()
+            else:
+                relationship.create(
+                    document_type=self.initial['document_type'],
+                    metadata_type=self.initial['metadata_type'], required=True
+                )
+
+
+DocumentTypeMetadataTypeRelationshipFormSet = formset_factory(
+    DocumentTypeMetadataTypeRelationshipForm, extra=0
+)
diff --git a/mayan/apps/metadata/links.py b/mayan/apps/metadata/links.py
index 1750dcef35..a1e841ef7a 100644
--- a/mayan/apps/metadata/links.py
+++ b/mayan/apps/metadata/links.py
@@ -36,15 +36,17 @@ link_metadata_remove = Link(
 )
 link_metadata_view = Link(
     icon='fa fa-pencil', permissions=(permission_metadata_document_view,),
-    text=_('Metadata'), view='metadata:metadata_view', args='resolved_object.pk'
+    text=_('Metadata'), view='metadata:metadata_view',
+    args='resolved_object.pk'
 )
-link_setup_document_type_metadata = Link(
-    permissions=(permission_document_type_edit,), text=_('Optional metadata'),
-    view='metadata:setup_document_type_metadata', args='resolved_object.pk'
+link_setup_document_type_metadata_types = Link(
+    permissions=(permission_document_type_edit,), text=_('Metadata types'),
+    view='metadata:setup_document_type_metadata_types',
+    args='resolved_object.pk'
 )
-link_setup_document_type_metadata_required = Link(
-    permissions=(permission_document_type_edit,), text=_('Required metadata'),
-    view='metadata:setup_document_type_metadata_required',
+link_setup_metadata_type_document_types = Link(
+    permissions=(permission_document_type_edit,), text=_('Document types'),
+    view='metadata:setup_metadata_type_document_types',
     args='resolved_object.pk'
 )
 link_setup_metadata_type_create = Link(
diff --git a/mayan/apps/metadata/migrations/0007_auto_20150918_0800.py b/mayan/apps/metadata/migrations/0007_auto_20150918_0800.py
index 7cf3016c2b..c5abfc9641 100644
--- a/mayan/apps/metadata/migrations/0007_auto_20150918_0800.py
+++ b/mayan/apps/metadata/migrations/0007_auto_20150918_0800.py
@@ -14,7 +14,22 @@ class Migration(migrations.Migration):
         migrations.AlterField(
             model_name='metadatatype',
             name='parser',
-            field=models.CharField(blank=True, help_text='The parser will reformat the value entered to conform to the expected format.', max_length=64, verbose_name='Parser', choices=[(b'metadata.parsers.DateAndTimeParser', b'metadata.parsers.DateAndTimeParser'), (b'metadata.parsers.DateParser', b'metadata.parsers.DateParser'), (b'metadata.parsers.TimeParser', b'metadata.parsers.TimeParser')]),
-            preserve_default=True,
+            field=models.CharField(
+                blank=True, help_text='The parser will reformat the value '
+                'entered to conform to the expected format.', max_length=64,
+                verbose_name='Parser',
+                choices=[
+                    (
+                        b'metadata.parsers.DateAndTimeParser',
+                        b'metadata.parsers.DateAndTimeParser'
+                    ), (
+                        b'metadata.parsers.DateParser',
+                        b'metadata.parsers.DateParser'
+                    ), (
+                        b'metadata.parsers.TimeParser',
+                        b'metadata.parsers.TimeParser'
+                    )
+                ]
+            ), preserve_default=True,
         ),
     ]
diff --git a/mayan/apps/metadata/urls.py b/mayan/apps/metadata/urls.py
index 658368c25e..52360725ae 100644
--- a/mayan/apps/metadata/urls.py
+++ b/mayan/apps/metadata/urls.py
@@ -11,8 +11,8 @@ from .views import (
     DocumentMetadataAddView, DocumentMetadataEditView,
     DocumentMetadataListView, DocumentMetadataRemoveView,
     MetadataTypeCreateView, MetadataTypeDeleteView, MetadataTypeEditView,
-    MetadataTypeListView, SetupDocumentTypeMetadataOptionalView,
-    SetupDocumentTypeMetadataRequiredView
+    MetadataTypeListView, SetupDocumentTypeMetadataTypes,
+    SetupMetadataTypesDocumentTypes
 )
 
 urlpatterns = [
@@ -61,16 +61,15 @@ urlpatterns = [
         r'^setup/type/(?P<pk>\d+)/delete/$',
         MetadataTypeDeleteView.as_view(), name='setup_metadata_type_delete'
     ),
-
     url(
-        r'^setup/document/type/(?P<pk>\d+)/metadata/edit/$',
-        SetupDocumentTypeMetadataOptionalView.as_view(),
-        name='setup_document_type_metadata'
+        r'^setup/document_types/(?P<pk>\d+)/metadata_types/$',
+        SetupDocumentTypeMetadataTypes.as_view(),
+        name='setup_document_type_metadata_types'
     ),
     url(
-        r'^setup/document/type/(?P<pk>\d+)/metadata/edit/required/$',
-        SetupDocumentTypeMetadataRequiredView.as_view(),
-        name='setup_document_type_metadata_required'
+        r'^setup/metadata_types/(?P<pk>\d+)/document_types/$',
+        SetupMetadataTypesDocumentTypes.as_view(),
+        name='setup_metadata_type_document_types'
     ),
 ]
 
diff --git a/mayan/apps/metadata/views.py b/mayan/apps/metadata/views.py
index a37007978b..8ddc570f1f 100644
--- a/mayan/apps/metadata/views.py
+++ b/mayan/apps/metadata/views.py
@@ -12,7 +12,7 @@ from django.utils.translation import ugettext_lazy as _, ungettext
 
 from acls.models import AccessControlList
 from common.generics import (
-    AssignRemoveView, MultipleObjectFormActionView, SingleObjectCreateView,
+    FormView, MultipleObjectFormActionView, SingleObjectCreateView,
     SingleObjectDeleteView, SingleObjectEditView, SingleObjectListView
 )
 from documents.models import Document, DocumentType
@@ -23,7 +23,8 @@ from documents.permissions import (
 from .api import save_metadata_list
 from .forms import (
     DocumentAddMetadataForm, DocumentMetadataFormSet,
-    DocumentMetadataRemoveFormSet, MetadataTypeForm
+    DocumentMetadataRemoveFormSet,
+    DocumentTypeMetadataTypeRelationshipFormSet, MetadataTypeForm
 )
 from .models import DocumentMetadata, MetadataType
 from .permissions import (
@@ -44,7 +45,9 @@ class DocumentMetadataAddView(MultipleObjectFormActionView):
     )
 
     def dispatch(self, request, *args, **kwargs):
-        result = super(DocumentMetadataAddView, self).dispatch(request, *args, **kwargs)
+        result = super(
+            DocumentMetadataAddView, self
+        ).dispatch(request, *args, **kwargs)
 
         queryset = self.get_queryset()
 
@@ -198,7 +201,9 @@ class DocumentMetadataEditView(MultipleObjectFormActionView):
     )
 
     def dispatch(self, request, *args, **kwargs):
-        result = super(DocumentMetadataEditView, self).dispatch(request, *args, **kwargs)
+        result = super(
+            DocumentMetadataEditView, self
+        ).dispatch(request, *args, **kwargs)
 
         queryset = self.get_queryset()
 
@@ -274,7 +279,9 @@ class DocumentMetadataEditView(MultipleObjectFormActionView):
             document.add_as_recent_document_for_user(self.request.user)
 
             for document_metadata in document.metadata.all():
-                metadata_dict.setdefault(document_metadata.metadata_type, set())
+                metadata_dict.setdefault(
+                    document_metadata.metadata_type, set()
+                )
 
                 if document_metadata.value:
                     metadata_dict[
@@ -364,7 +371,9 @@ class DocumentMetadataRemoveView(MultipleObjectFormActionView):
     )
 
     def dispatch(self, request, *args, **kwargs):
-        result = super(DocumentMetadataRemoveView, self).dispatch(request, *args, **kwargs)
+        result = super(
+            DocumentMetadataRemoveView, self
+        ).dispatch(request, *args, **kwargs)
 
         queryset = self.get_queryset()
 
@@ -543,59 +552,87 @@ class MetadataTypeListView(SingleObjectListView):
         }
 
 
-class SetupDocumentTypeMetadataOptionalView(AssignRemoveView):
-    decode_content_type = True
+class SetupDocumentTypeMetadataTypes(FormView):
+    form_class = DocumentTypeMetadataTypeRelationshipFormSet
+    main_model = 'document_type'
+    model = DocumentType
+    submodel = MetadataType
     view_permission = permission_document_type_edit
-    left_list_title = _('Available metadata types')
-    right_list_title = _('Metadata types assigned')
 
-    def add(self, item):
-        self.get_object().metadata.create(metadata_type=item, required=False)
+    def form_valid(self, form):
+        try:
+            for instance in form:
+                instance.save()
+        except Exception as exception:
+            messages.error(
+                self.request,
+                _('Error updating relationship; %s') % exception
+            )
+        else:
+            messages.success(
+                self.request, _('Relationships updated successfully')
+            )
+
+        return super(
+            SetupDocumentTypeMetadataTypes, self
+        ).form_valid(form=form)
 
     def get_object(self):
-        return get_object_or_404(DocumentType, pk=self.kwargs['pk'])
-
-    def left_list(self):
-        return AssignRemoveView.generate_choices(
-            set(MetadataType.objects.all()) - set(
-                MetadataType.objects.filter(
-                    id__in=self.get_object().metadata.values_list(
-                        'metadata_type', flat=True
-                    )
-                )
-            )
-        )
-
-    def right_list(self):
-        return AssignRemoveView.generate_choices(
-            self.get_object().metadata.filter(required=False)
-        )
-
-    def remove(self, item):
-        item.delete()
+        return get_object_or_404(self.model, pk=self.kwargs['pk'])
 
     def get_extra_context(self):
         return {
+            'form_display_mode_table': True,
             'object': self.get_object(),
             'title': _(
-                'Optional metadata types for document type: %s'
-            ) % self.get_object(),
+                'Metadata types for document type: %s'
+            ) % self.get_object()
         }
 
+    def get_initial(self):
+        obj = self.get_object()
+        initial = []
 
-class SetupDocumentTypeMetadataRequiredView(SetupDocumentTypeMetadataOptionalView):
-    def add(self, item):
-        self.get_object().metadata.create(metadata_type=item, required=True)
+        for element in self.get_queryset():
+            initial.append({
+                'document_type': obj,
+                'main_model': self.main_model,
+                'metadata_type': element,
+            })
+        return initial
 
-    def right_list(self):
-        return AssignRemoveView.generate_choices(
-            self.get_object().metadata.filter(required=True)
-        )
+    def get_post_action_redirect(self):
+        return reverse('documents:document_type_list')
+
+    def get_queryset(self):
+        return self.submodel.objects.all()
+
+
+class SetupMetadataTypesDocumentTypes(SetupDocumentTypeMetadataTypes):
+    main_model = 'metadata_type'
+    model = MetadataType
+    submodel = DocumentType
 
     def get_extra_context(self):
         return {
+            'form_display_mode_table': True,
             'object': self.get_object(),
             'title': _(
-                'Required metadata types for document type: %s'
-            ) % self.get_object(),
+                'Document types for metadata type: %s'
+            ) % self.get_object()
         }
+
+    def get_initial(self):
+        obj = self.get_object()
+        initial = []
+
+        for element in self.get_queryset():
+            initial.append({
+                'document_type': element,
+                'main_model': self.main_model,
+                'metadata_type': obj,
+            })
+        return initial
+
+    def get_post_action_redirect(self):
+        return reverse('metadata:setup_metadata_type_list')