diff --git a/InvenTree/InvenTree/api_version.py b/InvenTree/InvenTree/api_version.py
index 14c180388cff..d272ac54e69e 100644
--- a/InvenTree/InvenTree/api_version.py
+++ b/InvenTree/InvenTree/api_version.py
@@ -2,11 +2,15 @@
 
 
 # InvenTree API version
-INVENTREE_API_VERSION = 139
+INVENTREE_API_VERSION = 140
 
 """
 Increment this API version number whenever there is a significant change to the API that any clients need to know about
 
+v140 -> 2023-10-20 : https://github.com/inventree/InvenTree/pull/5664
+    - Expand API token functionality
+    - Multiple API tokens can be generated per user
+
 v139 -> 2023-10-11 : https://github.com/inventree/InvenTree/pull/5509
     - Add new BarcodePOReceive endpoint to receive line items by scanning supplier barcodes
 
diff --git a/InvenTree/InvenTree/middleware.py b/InvenTree/InvenTree/middleware.py
index 6a365d82de8c..c34c5416e8ef 100644
--- a/InvenTree/InvenTree/middleware.py
+++ b/InvenTree/InvenTree/middleware.py
@@ -12,9 +12,9 @@
 from allauth_2fa.middleware import (AllauthTwoFactorMiddleware,
                                     BaseRequire2FAMiddleware)
 from error_report.middleware import ExceptionProcessor
-from rest_framework.authtoken.models import Token
 
 from InvenTree.urls import frontendpatterns
+from users.models import ApiToken
 
 logger = logging.getLogger("inventree")
 
@@ -75,13 +75,15 @@ def __call__(self, request):
 
                     # Does the provided token match a valid user?
                     try:
-                        token = Token.objects.get(key=token_key)
+                        token = ApiToken.objects.get(key=token_key)
 
-                        # Provide the user information to the request
-                        request.user = token.user
-                        authorized = True
+                        if token.active and token.user:
 
-                    except Token.DoesNotExist:
+                            # Provide the user information to the request
+                            request.user = token.user
+                            authorized = True
+
+                    except ApiToken.DoesNotExist:
                         logger.warning("Access denied for unknown token %s", token_key)
 
             # No authorization was found for the request
diff --git a/InvenTree/InvenTree/settings.py b/InvenTree/InvenTree/settings.py
index 32f6ebfc35d3..5630adf28272 100644
--- a/InvenTree/InvenTree/settings.py
+++ b/InvenTree/InvenTree/settings.py
@@ -232,7 +232,6 @@
     # Third part add-ons
     'django_filters',                       # Extended filter functionality
     'rest_framework',                       # DRF (Django Rest Framework)
-    'rest_framework.authtoken',             # Token authentication for API
     'corsheaders',                          # Cross-origin Resource Sharing for DRF
     'crispy_forms',                         # Improved form rendering
     'import_export',                        # Import / export tables to file
@@ -433,7 +432,7 @@
     'DEFAULT_AUTHENTICATION_CLASSES': (
         'rest_framework.authentication.BasicAuthentication',
         'rest_framework.authentication.SessionAuthentication',
-        'rest_framework.authentication.TokenAuthentication',
+        'users.authentication.ApiTokenAuthentication',
     ),
     'DEFAULT_PAGINATION_CLASS': 'rest_framework.pagination.LimitOffsetPagination',
     'DEFAULT_PERMISSION_CLASSES': (
@@ -445,7 +444,8 @@
     'DEFAULT_METADATA_CLASS': 'InvenTree.metadata.InvenTreeMetadata',
     'DEFAULT_RENDERER_CLASSES': [
         'rest_framework.renderers.JSONRenderer',
-    ]
+    ],
+    'TOKEN_MODEL': 'users.models.ApiToken',
 }
 
 if DEBUG:
diff --git a/InvenTree/users/admin.py b/InvenTree/users/admin.py
index be7cf646afb3..a63100a5c3f3 100644
--- a/InvenTree/users/admin.py
+++ b/InvenTree/users/admin.py
@@ -9,11 +9,26 @@
 from django.utils.safestring import mark_safe
 from django.utils.translation import gettext_lazy as _
 
-from users.models import Owner, RuleSet
+from users.models import ApiToken, Owner, RuleSet
 
 User = get_user_model()
 
 
+class ApiTokenAdmin(admin.ModelAdmin):
+    """Admin class for the ApiToken model."""
+
+    list_display = ('token', 'user', 'name', 'expiry', 'active')
+    fields = ('token', 'user', 'name', 'revoked', 'expiry')
+
+    def get_readonly_fields(self, request, obj=None):
+        """Some fields are read-only after creation"""
+
+        if obj:
+            return ['token', 'user', 'expiry', 'name']
+        else:
+            return ['token']
+
+
 class RuleSetInline(admin.TabularInline):
     """Class for displaying inline RuleSet data in the Group admin page."""
 
@@ -239,3 +254,5 @@ class OwnerAdmin(admin.ModelAdmin):
 admin.site.register(User, InvenTreeUserAdmin)
 
 admin.site.register(Owner, OwnerAdmin)
+
+admin.site.register(ApiToken, ApiTokenAdmin)
diff --git a/InvenTree/users/api.py b/InvenTree/users/api.py
index 688b301fad53..51fd19314215 100644
--- a/InvenTree/users/api.py
+++ b/InvenTree/users/api.py
@@ -1,21 +1,23 @@
 """DRF API definition for the 'users' app"""
 
+import logging
+
 from django.contrib.auth.models import Group, User
-from django.core.exceptions import ObjectDoesNotExist
 from django.urls import include, path, re_path
 
 from django_filters.rest_framework import DjangoFilterBackend
-from rest_framework import permissions, status
-from rest_framework.authtoken.models import Token
+from rest_framework import exceptions, permissions
 from rest_framework.response import Response
 from rest_framework.views import APIView
 
 from InvenTree.filters import InvenTreeSearchFilter
 from InvenTree.mixins import ListAPI, RetrieveAPI, RetrieveUpdateAPI
 from InvenTree.serializers import UserSerializer
-from users.models import Owner, RuleSet, check_user_role
+from users.models import ApiToken, Owner, RuleSet, check_user_role
 from users.serializers import GroupSerializer, OwnerSerializer
 
+logger = logging.getLogger('inventree')
+
 
 class OwnerList(ListAPI):
     """List API endpoint for Owner model.
@@ -187,25 +189,34 @@ class GetAuthToken(APIView):
     def get(self, request, *args, **kwargs):
         """Return an API token if the user is authenticated
 
-        - If the user already has a token, return it
-        - Otherwise, create a new token
+        - If the user already has a matching token, delete it and create a new one
+        - Existing tokens are *never* exposed again via the API
+        - Once the token is provided, it can be used for auth until it expires
         """
+
         if request.user.is_authenticated:
-            # Get the user token (or create one if it does not exist)
-            token, created = Token.objects.get_or_create(user=request.user)
-            return Response({
+
+            user = request.user
+            name = request.query_params.get('name', '')
+
+            # Delete any matching tokens
+            ApiToken.objects.filter(user=user, name=name).delete()
+
+            # User is authenticated, and requesting a token against the provided name.
+            token = ApiToken.objects.create(user=request.user, name=name)
+
+            data = {
                 'token': token.key,
-            })
-
-    def delete(self, request):
-        """User has requested deletion of API token"""
-        try:
-            request.user.auth_token.delete()
-            return Response({"success": "Successfully logged out."},
-                            status=status.HTTP_202_ACCEPTED)
-        except (AttributeError, ObjectDoesNotExist):
-            return Response({"error": "Bad request"},
-                            status=status.HTTP_400_BAD_REQUEST)
+                'name': token.name,
+                'expiry': token.expiry,
+            }
+
+            logger.info("Created new API token for user '%s' (name='%s')", user.username, name)
+
+            return Response(data)
+
+        else:
+            raise exceptions.NotAuthenticated()
 
 
 user_urls = [
diff --git a/InvenTree/users/authentication.py b/InvenTree/users/authentication.py
new file mode 100644
index 000000000000..82d02a998204
--- /dev/null
+++ b/InvenTree/users/authentication.py
@@ -0,0 +1,32 @@
+"""Custom token authentication class for InvenTree API"""
+
+from django.utils.translation import gettext_lazy as _
+
+from rest_framework import exceptions
+from rest_framework.authentication import TokenAuthentication
+
+from users.models import ApiToken
+
+
+class ApiTokenAuthentication(TokenAuthentication):
+    """Custom implementation of TokenAuthentication class, with custom features:
+
+    - Tokens can be revoked
+    - Tokens can expire
+    """
+
+    model = ApiToken
+
+    def authenticate_credentials(self, key):
+        """Adds additional checks to the default token authentication method."""
+
+        # If this runs without error, then the token is valid (so far)
+        (user, token) = super().authenticate_credentials(key)
+
+        if token.revoked:
+            raise exceptions.AuthenticationFailed(_("Token has been revoked"))
+
+        if token.expired:
+            raise exceptions.AuthenticationFailed(_("Token has expired"))
+
+        return (user, token)
diff --git a/InvenTree/users/migrations/0008_apitoken.py b/InvenTree/users/migrations/0008_apitoken.py
new file mode 100644
index 000000000000..52c4cc7edf1a
--- /dev/null
+++ b/InvenTree/users/migrations/0008_apitoken.py
@@ -0,0 +1,35 @@
+# Generated by Django 3.2.22 on 2023-10-20 01:09
+
+from django.conf import settings
+from django.db import migrations, models
+import django.db.models.deletion
+import users.models
+
+
+class Migration(migrations.Migration):
+
+    dependencies = [
+        migrations.swappable_dependency(settings.AUTH_USER_MODEL),
+        ('users', '0007_alter_ruleset_name'),
+    ]
+
+    operations = [
+        migrations.CreateModel(
+            name='ApiToken',
+            fields=[
+                ('id', models.AutoField(auto_created=True, primary_key=True, serialize=False, verbose_name='ID')),
+                ('created', models.DateTimeField(auto_now_add=True, verbose_name='Created')),
+                ('key', models.CharField(db_index=True, default=users.models.default_token, max_length=100, unique=True, verbose_name='Key')),
+                ('name', models.CharField(blank=True, help_text='Custom token name', max_length=100, verbose_name='Token Name')),
+                ('expiry', models.DateField(default=users.models.default_token_expiry, help_text='Token expiry date', verbose_name='Expiry Date')),
+                ('revoked', models.BooleanField(default=False, help_text='Token has been revoked', verbose_name='Revoked')),
+                ('user', models.ForeignKey(on_delete=django.db.models.deletion.CASCADE, related_name='api_tokens', to=settings.AUTH_USER_MODEL, verbose_name='User')),
+            ],
+            options={
+                'verbose_name': 'API Token',
+                'verbose_name_plural': 'API Tokens',
+                'abstract': False,
+                'unique_together': {('user', 'name')},
+            },
+        ),
+    ]
diff --git a/InvenTree/users/models.py b/InvenTree/users/models.py
index 89f619d6353a..a7eb4cd01631 100644
--- a/InvenTree/users/models.py
+++ b/InvenTree/users/models.py
@@ -1,7 +1,10 @@
 """Database model definitions for the 'users' app"""
 
+import datetime
 import logging
 
+from django.conf import settings
+from django.contrib import admin
 from django.contrib.auth import get_user_model
 from django.contrib.auth.models import Group, Permission
 from django.contrib.contenttypes.fields import GenericForeignKey
@@ -15,11 +18,115 @@
 from django.urls import reverse
 from django.utils.translation import gettext_lazy as _
 
+from rest_framework.authtoken.models import Token as AuthToken
+
 from InvenTree.ready import canAppAccessDatabase
 
 logger = logging.getLogger("inventree")
 
 
+def default_token():
+    """Generate a default value for the token"""
+    return ApiToken.generate_key()
+
+
+def default_token_expiry():
+    """Generate an expiry date for a newly created token"""
+
+    # TODO: Custom value for default expiry timeout
+    # TODO: For now, tokens last for 1 year
+    return datetime.datetime.now().date() + datetime.timedelta(days=365)
+
+
+class ApiToken(AuthToken):
+    """Extends the default token model provided by djangorestframework.authtoken, as follows:
+
+    - Adds an 'expiry' date - tokens can be set to expire after a certain date
+    - Adds a 'name' field - tokens can be given a custom name (in addition to the user information)
+    """
+
+    class Meta:
+        """Metaclass defines model properties"""
+        verbose_name = _('API Token')
+        verbose_name_plural = _('API Tokens')
+        abstract = False
+        unique_together = [
+            ('user', 'name')
+        ]
+
+    def __str__(self):
+        """String representation uses the redacted token"""
+        return self.token
+
+    @classmethod
+    def generate_key(cls, prefix='inv-'):
+        """Generate a new token key - with custom prefix"""
+
+        # Suffix is the date of creation
+        suffix = '-' + str(datetime.datetime.now().date().isoformat().replace('-', ''))
+
+        return prefix + str(AuthToken.generate_key()) + suffix
+
+    # Override the 'key' field - force it to be unique
+    key = models.CharField(default=default_token, verbose_name=_('Key'), max_length=100, db_index=True, unique=True)
+
+    # Override the 'user' field, to allow multiple tokens per user
+    user = models.ForeignKey(
+        settings.AUTH_USER_MODEL,
+        on_delete=models.CASCADE,
+        verbose_name=_('User'),
+        related_name='api_tokens',
+    )
+
+    name = models.CharField(
+        max_length=100,
+        blank=True,
+        verbose_name=_('Token Name'),
+        help_text=_('Custom token name'),
+    )
+
+    expiry = models.DateField(
+        default=default_token_expiry,
+        verbose_name=_('Expiry Date'),
+        help_text=_('Token expiry date'),
+        auto_now=False, auto_now_add=False,
+    )
+
+    revoked = models.BooleanField(
+        default=False,
+        verbose_name=_('Revoked'),
+        help_text=_('Token has been revoked'),
+    )
+
+    @property
+    @admin.display(description=_('Token'))
+    def token(self):
+        """Provide a redacted version of the token.
+
+        The *raw* key value should never be displayed anywhere!
+        """
+
+        # If the token has not yet been saved, return the raw key
+        if self.pk is None:
+            return self.key
+
+        M = len(self.key) - 20
+
+        return self.key[:8] + '*' * M + self.key[-12:]
+
+    @property
+    @admin.display(boolean=True, description=_('Expired'))
+    def expired(self):
+        """Test if this token has expired"""
+        return self.expiry is not None and self.expiry < datetime.datetime.now().date()
+
+    @property
+    @admin.display(boolean=True, description=_('Active'))
+    def active(self):
+        """Test if this token is active"""
+        return not self.revoked and not self.expired
+
+
 class RuleSet(models.Model):
     """A RuleSet is somewhat like a superset of the django permission class, in that in encapsulates a bunch of permissions.
 
@@ -58,8 +165,7 @@ class RuleSet(models.Model):
             'auth_group',
             'auth_user',
             'auth_permission',
-            'authtoken_token',
-            'authtoken_tokenproxy',
+            'users_apitoken',
             'users_ruleset',
             'report_reportasset',
             'report_reportsnippet',
diff --git a/InvenTree/users/test_api.py b/InvenTree/users/test_api.py
index d22a2ada7bbb..94da4b5ead22 100644
--- a/InvenTree/users/test_api.py
+++ b/InvenTree/users/test_api.py
@@ -1,9 +1,12 @@
 """API tests for various user / auth API endpoints"""
 
+import datetime
+
 from django.contrib.auth.models import Group, User
 from django.urls import reverse
 
 from InvenTree.unit_test import InvenTreeAPITestCase
+from users.models import ApiToken
 
 
 class UserAPITests(InvenTreeAPITestCase):
@@ -51,3 +54,82 @@ def test_group_api(self):
         )
 
         self.assertIn('name', response.data)
+
+
+class UserTokenTests(InvenTreeAPITestCase):
+    """Tests for user token functionality"""
+
+    def test_token_generation(self):
+        """Test user token generation"""
+
+        url = reverse('api-token')
+
+        self.assertEqual(ApiToken.objects.count(), 0)
+
+        # Generate multiple tokens with different names
+        for name in ['cat', 'dog', 'biscuit']:
+            data = self.get(url, data={'name': name}, expected_code=200).data
+
+            self.assertTrue(data['token'].startswith('inv-'))
+            self.assertEqual(data['name'], name)
+
+        # Check that the tokens were created
+        self.assertEqual(ApiToken.objects.count(), 3)
+
+        # If we re-generate a token, the value changes
+        token = ApiToken.objects.filter(name='cat').first()
+
+        # Request a *new* token with the same name
+        data = self.get(url, data={'name': 'cat'}, expected_code=200).data
+
+        self.assertNotEqual(data['token'], token.key)
+
+        # Check the old token is deleted
+        self.assertEqual(ApiToken.objects.count(), 3)
+        with self.assertRaises(ApiToken.DoesNotExist):
+            token.refresh_from_db()
+
+    def test_token_auth(self):
+        """Test user token authentication"""
+
+        # Create a new token
+        token_key = self.get(url=reverse('api-token'), data={'name': 'test'}, expected_code=200).data['token']
+
+        # Check that we can use the token to authenticate
+        self.client.logout()
+        self.client.credentials(HTTP_AUTHORIZATION='Token ' + token_key)
+
+        me = reverse('api-user-me')
+
+        response = self.client.get(me, expected_code=200)
+
+        # Grab the token, and update
+        token = ApiToken.objects.first()
+        self.assertEqual(token.key, token_key)
+
+        # Revoke the token
+        token.revoked = True
+        token.save()
+
+        self.assertFalse(token.active)
+
+        response = self.client.get(me, expected_code=401)
+        self.assertIn('Token has been revoked', str(response.data))
+
+        # Expire the token
+        token.revoked = False
+        token.expiry = datetime.datetime.now().date() - datetime.timedelta(days=10)
+        token.save()
+
+        self.assertTrue(token.expired)
+        self.assertFalse(token.active)
+
+        response = self.client.get(me, expected_code=401)
+        self.assertIn('Token has expired', str(response.data))
+
+        # Re-enable the token
+        token.revoked = False
+        token.expiry = datetime.datetime.now().date() + datetime.timedelta(days=10)
+        token.save()
+
+        self.client.get(me, expected_code=200)
diff --git a/InvenTree/users/tests.py b/InvenTree/users/tests.py
index 2158209cf577..de1c443ef57e 100644
--- a/InvenTree/users/tests.py
+++ b/InvenTree/users/tests.py
@@ -5,10 +5,8 @@
 from django.test import TestCase
 from django.urls import reverse
 
-from rest_framework.authtoken.models import Token
-
 from InvenTree.unit_test import InvenTreeTestCase
-from users.models import Owner, RuleSet
+from users.models import ApiToken, Owner, RuleSet
 
 
 class RuleSetModelTest(TestCase):
@@ -242,7 +240,7 @@ def test_token(self):
         """Test token mechanisms."""
         self.client.logout()
 
-        token = Token.objects.filter(user=self.user)
+        token = ApiToken.objects.filter(user=self.user)
 
         # not authed
         self.do_request(reverse('api-token'), {}, 401)
@@ -252,15 +250,6 @@ def test_token(self):
         response = self.do_request(reverse('api-token'), {})
         self.assertEqual(response['token'], token.first().key)
 
-        # token delete
-        response = self.client.delete(reverse('api-token'), {}, format='json')
-        self.assertEqual(response.status_code, 202)
-        self.assertEqual(len(token), 0)
-
-        # token second delete
-        response = self.client.delete(reverse('api-token'), {}, format='json')
-        self.assertEqual(response.status_code, 400)
-
         # test user is associated with token
-        response = self.do_request(reverse('api-user-me'), {}, 200)
+        response = self.do_request(reverse('api-user-me'), {'name': 'another-token'}, 200)
         self.assertEqual(response['username'], self.username)
diff --git a/src/frontend/src/components/nav/NotificationDrawer.tsx b/src/frontend/src/components/nav/NotificationDrawer.tsx
index e546d16d93c8..c9da406adcfe 100644
--- a/src/frontend/src/components/nav/NotificationDrawer.tsx
+++ b/src/frontend/src/components/nav/NotificationDrawer.tsx
@@ -81,12 +81,12 @@ export function NotificationDrawer({
       <Stack spacing="xs">
         <Divider />
         <LoadingOverlay visible={notificationQuery.isFetching} />
-        {notificationQuery.data?.results?.length == 0 && (
+        {(notificationQuery.data?.results?.length ?? 0) == 0 && (
           <Alert color="green">
             <Text size="sm">{t`You have no unread notifications.`}</Text>
           </Alert>
         )}
-        {notificationQuery.data?.results.map((notification: any) => (
+        {notificationQuery.data?.results?.map((notification: any) => (
           <Group position="apart">
             <Stack spacing="3">
               <Text size="sm">{notification.target?.name ?? 'target'}</Text>
diff --git a/src/frontend/src/functions/auth.tsx b/src/frontend/src/functions/auth.tsx
index d76813872069..9f7a3657f86a 100644
--- a/src/frontend/src/functions/auth.tsx
+++ b/src/frontend/src/functions/auth.tsx
@@ -21,7 +21,10 @@ export const doClassicLogin = async (username: string, password: string) => {
     .get(apiUrl(ApiPaths.user_token), {
       auth: { username, password },
       baseURL: host.toString(),
-      timeout: 5000
+      timeout: 5000,
+      params: {
+        name: 'inventree-web-app'
+      }
     })
     .then((response) => response.data.token)
     .catch((error) => {
@@ -114,7 +117,10 @@ export function handleReset(navigate: any, values: { email: string }) {
 export function checkLoginState(navigate: any, redirect?: string) {
   api
     .get(apiUrl(ApiPaths.user_token), {
-      timeout: 5000
+      timeout: 5000,
+      params: {
+        name: 'inventree-web-app'
+      }
     })
     .then((val) => {
       if (val.status === 200 && val.data.token) {
diff --git a/tasks.py b/tasks.py
index 8bd97d6ad349..03f11ad24f1e 100644
--- a/tasks.py
+++ b/tasks.py
@@ -35,7 +35,7 @@ def content_excludes():
     excludes = [
         "contenttypes",
         "auth.permission",
-        "authtoken.token",
+        "users.apitoken",
         "error_report.error",
         "admin.logentry",
         "django_q.schedule",