diff --git a/tests/functional/test_login.py b/tests/functional/test_login.py
index 78d991025f65..31140a07b27b 100644
--- a/tests/functional/test_login.py
+++ b/tests/functional/test_login.py
@@ -49,7 +49,7 @@ def test_unrecognized_login_with_totp(webtest):
     assert resp.status_code == HTTPStatus.SEE_OTHER
     assert resp.headers["Location"].endswith("/account/confirm-login/")
     unrecognized_page = resp.follow()
-    assert "Unrecognized device" in unrecognized_page
+    assert "Please confirm this login" in unrecognized_page
 
     # This is a hack because the functional test doesn't have another way to
     # determine the magic link that was sent in the email. Instead, find the
diff --git a/tests/unit/accounts/test_views.py b/tests/unit/accounts/test_views.py
index 50c453a45ad0..0f4ca50c2123 100644
--- a/tests/unit/accounts/test_views.py
+++ b/tests/unit/accounts/test_views.py
@@ -5443,70 +5443,6 @@ def test_user_not_found(self, pyramid_request):
             pretend.call("Invalid token: user not found", queue="error")
         ]
 
-    def test_user_logged_in_since_naive_datetime(self, db_request):
-        user = UserFactory.create(last_login=datetime.datetime.now(datetime.UTC))
-        db_request.user = None
-        db_request.params = {"token": "foo"}
-        token_data = {
-            "action": "login-confirmation",
-            "user.id": str(user.id),
-            "user.last_login": (user.last_login - datetime.timedelta(seconds=1))
-            .replace(tzinfo=None)
-            .isoformat(),
-        }
-        token_service = pretend.stub(loads=pretend.call_recorder(lambda t: token_data))
-        user_service = pretend.stub(get_user=pretend.call_recorder(lambda uid: user))
-
-        db_request.find_service = lambda interface, name=None, **kwargs: {
-            ITokenService: {"confirm_login": token_service},
-            IUserService: {None: user_service},
-        }[interface][name]
-        db_request.session.flash = pretend.call_recorder(lambda *a, **kw: None)
-        db_request.route_path = pretend.call_recorder(lambda r: f"/{r}")
-
-        result = views.confirm_login(db_request)
-
-        assert isinstance(result, HTTPSeeOther)
-        assert result.location == "/accounts.login"
-        assert db_request.session.flash.calls == [
-            pretend.call(
-                "Invalid token: user has logged in since this token was requested",
-                queue="error",
-            )
-        ]
-
-    def test_user_logged_in_since(self, db_request):
-        user = UserFactory.create(last_login=datetime.datetime.now(datetime.UTC))
-        db_request.user = None
-        db_request.params = {"token": "foo"}
-        token_data = {
-            "action": "login-confirmation",
-            "user.id": str(user.id),
-            "user.last_login": (
-                user.last_login - datetime.timedelta(seconds=1)
-            ).isoformat(),
-        }
-        token_service = pretend.stub(loads=pretend.call_recorder(lambda t: token_data))
-        user_service = pretend.stub(get_user=pretend.call_recorder(lambda uid: user))
-
-        db_request.find_service = lambda interface, name=None, **kwargs: {
-            ITokenService: {"confirm_login": token_service},
-            IUserService: {None: user_service},
-        }[interface][name]
-        db_request.session.flash = pretend.call_recorder(lambda *a, **kw: None)
-        db_request.route_path = pretend.call_recorder(lambda r: f"/{r}")
-
-        result = views.confirm_login(db_request)
-
-        assert isinstance(result, HTTPSeeOther)
-        assert result.location == "/accounts.login"
-        assert db_request.session.flash.calls == [
-            pretend.call(
-                "Invalid token: user has logged in since this token was requested",
-                queue="error",
-            )
-        ]
-
     def test_unique_login_not_found(self, db_request):
         user = UserFactory.create(last_login=datetime.datetime.now(datetime.UTC))
         db_request.user = None
diff --git a/warehouse/accounts/models.py b/warehouse/accounts/models.py
index c97bdc43a9ff..b518536e7051 100644
--- a/warehouse/accounts/models.py
+++ b/warehouse/accounts/models.py
@@ -122,7 +122,10 @@ class User(SitemapMixin, HasObservers, HasObservations, HasEvents, db.Model):
     )
 
     unique_logins: Mapped[list[UserUniqueLogin]] = orm.relationship(
-        back_populates="user", cascade="all, delete-orphan", lazy=True
+        back_populates="user",
+        cascade="all, delete-orphan",
+        lazy=True,
+        order_by="UserUniqueLogin.created.desc()",
     )
 
     role_invitations: Mapped[list[RoleInvitation]] = orm.relationship(
diff --git a/warehouse/accounts/views.py b/warehouse/accounts/views.py
index 3fe094a625a3..911ef201588e 100644
--- a/warehouse/accounts/views.py
+++ b/warehouse/accounts/views.py
@@ -1020,19 +1020,6 @@ def _error(message):
     if user is None:
         return _error(request._("Invalid token: user not found"))
 
-    # Check whether the user has logged in since the token was created
-    last_login = datetime.datetime.fromisoformat(data.get("user.last_login"))
-    # Before updating itsdangerous to 2.x the last_login was naive,
-    # now it's localized to UTC
-    if not last_login.tzinfo:
-        last_login = pytz.UTC.localize(last_login)
-    if user.last_login and user.last_login > last_login:
-        return _error(
-            request._(
-                "Invalid token: user has logged in since this token was requested"
-            )
-        )
-
     unique_login_id = data.get("unique_login_id")
     unique_login = (
         request.db.query(UserUniqueLogin)
diff --git a/warehouse/admin/views/ip_addresses.py b/warehouse/admin/views/ip_addresses.py
index aaa543b186f5..36ff64b2ce79 100644
--- a/warehouse/admin/views/ip_addresses.py
+++ b/warehouse/admin/views/ip_addresses.py
@@ -61,6 +61,7 @@ def ip_address_detail(request: Request) -> dict[str, IpAddress]:
     unique_logins = (
         request.db.query(UserUniqueLogin)
         .filter(UserUniqueLogin.ip_address == str(ip_address.ip_address))
+        .order_by(UserUniqueLogin.created.desc())
         .all()
     )
 
diff --git a/warehouse/locale/messages.pot b/warehouse/locale/messages.pot
index e4f89f323946..3ed82ff47bc4 100644
--- a/warehouse/locale/messages.pot
+++ b/warehouse/locale/messages.pot
@@ -183,8 +183,8 @@ msgid "Invalid token: request a new password reset link"
 msgstr ""
 
 #: warehouse/accounts/views.py:903 warehouse/accounts/views.py:1012
-#: warehouse/accounts/views.py:1090 warehouse/accounts/views.py:1196
-#: warehouse/accounts/views.py:1365
+#: warehouse/accounts/views.py:1077 warehouse/accounts/views.py:1183
+#: warehouse/accounts/views.py:1352
 msgid "Invalid token: no token supplied"
 msgstr ""
 
@@ -196,7 +196,7 @@ msgstr ""
 msgid "Invalid token: user not found"
 msgstr ""
 
-#: warehouse/accounts/views.py:923 warehouse/accounts/views.py:1032
+#: warehouse/accounts/views.py:923
 msgid "Invalid token: user has logged in since this token was requested"
 msgstr ""
 
@@ -222,123 +222,123 @@ msgstr ""
 msgid "Invalid token: not a login confirmation token"
 msgstr ""
 
-#: warehouse/accounts/views.py:1044
+#: warehouse/accounts/views.py:1031
 msgid "Invalid login attempt."
 msgstr ""
 
-#: warehouse/accounts/views.py:1049
+#: warehouse/accounts/views.py:1036
 msgid ""
 "Device details didn't match, please try again from the device you "
 "originally used to log in."
 msgstr ""
 
-#: warehouse/accounts/views.py:1060
+#: warehouse/accounts/views.py:1047
 msgid "Your login has been confirmed and this device is now recognized."
 msgstr ""
 
-#: warehouse/accounts/views.py:1086
+#: warehouse/accounts/views.py:1073
 msgid "Expired token: request a new email verification link"
 msgstr ""
 
-#: warehouse/accounts/views.py:1088
+#: warehouse/accounts/views.py:1075
 msgid "Invalid token: request a new email verification link"
 msgstr ""
 
-#: warehouse/accounts/views.py:1094
+#: warehouse/accounts/views.py:1081
 msgid "Invalid token: not an email verification token"
 msgstr ""
 
-#: warehouse/accounts/views.py:1103
+#: warehouse/accounts/views.py:1090
 msgid "Email not found"
 msgstr ""
 
-#: warehouse/accounts/views.py:1106
+#: warehouse/accounts/views.py:1093
 msgid "Email already verified"
 msgstr ""
 
-#: warehouse/accounts/views.py:1126
+#: warehouse/accounts/views.py:1113
 msgid "You can now set this email as your primary address"
 msgstr ""
 
-#: warehouse/accounts/views.py:1129
+#: warehouse/accounts/views.py:1116
 msgid "This is your primary address"
 msgstr ""
 
-#: warehouse/accounts/views.py:1135
+#: warehouse/accounts/views.py:1122
 #, python-brace-format
 msgid "Email address ${email_address} verified. ${confirm_message}."
 msgstr ""
 
-#: warehouse/accounts/views.py:1192
+#: warehouse/accounts/views.py:1179
 msgid "Expired token: request a new organization invitation"
 msgstr ""
 
-#: warehouse/accounts/views.py:1194
+#: warehouse/accounts/views.py:1181
 msgid "Invalid token: request a new organization invitation"
 msgstr ""
 
-#: warehouse/accounts/views.py:1200
+#: warehouse/accounts/views.py:1187
 msgid "Invalid token: not an organization invitation token"
 msgstr ""
 
-#: warehouse/accounts/views.py:1204
+#: warehouse/accounts/views.py:1191
 msgid "Organization invitation is not valid."
 msgstr ""
 
-#: warehouse/accounts/views.py:1213
+#: warehouse/accounts/views.py:1200
 msgid "Organization invitation no longer exists."
 msgstr ""
 
-#: warehouse/accounts/views.py:1265
+#: warehouse/accounts/views.py:1252
 #, python-brace-format
 msgid "Invitation for '${organization_name}' is declined."
 msgstr ""
 
-#: warehouse/accounts/views.py:1328
+#: warehouse/accounts/views.py:1315
 #, python-brace-format
 msgid "You are now ${role} of the '${organization_name}' organization."
 msgstr ""
 
-#: warehouse/accounts/views.py:1361
+#: warehouse/accounts/views.py:1348
 msgid "Expired token: request a new project role invitation"
 msgstr ""
 
-#: warehouse/accounts/views.py:1363
+#: warehouse/accounts/views.py:1350
 msgid "Invalid token: request a new project role invitation"
 msgstr ""
 
-#: warehouse/accounts/views.py:1369
+#: warehouse/accounts/views.py:1356
 msgid "Invalid token: not a collaboration invitation token"
 msgstr ""
 
-#: warehouse/accounts/views.py:1373
+#: warehouse/accounts/views.py:1360
 msgid "Role invitation is not valid."
 msgstr ""
 
-#: warehouse/accounts/views.py:1380
+#: warehouse/accounts/views.py:1367
 msgid "Invalid token: project does not exist"
 msgstr ""
 
-#: warehouse/accounts/views.py:1391
+#: warehouse/accounts/views.py:1378
 msgid "Role invitation no longer exists."
 msgstr ""
 
-#: warehouse/accounts/views.py:1423
+#: warehouse/accounts/views.py:1410
 #, python-brace-format
 msgid "Invitation for '${project_name}' is declined."
 msgstr ""
 
-#: warehouse/accounts/views.py:1489
+#: warehouse/accounts/views.py:1476
 #, python-brace-format
 msgid "You are now ${role} of the '${project_name}' project."
 msgstr ""
 
-#: warehouse/accounts/views.py:1601
+#: warehouse/accounts/views.py:1588
 #, python-brace-format
 msgid "Please review our updated <a href=\"${tos_url}\">Terms of Service</a>."
 msgstr ""
 
-#: warehouse/accounts/views.py:1813 warehouse/accounts/views.py:2067
+#: warehouse/accounts/views.py:1800 warehouse/accounts/views.py:2054
 #: warehouse/manage/views/oidc_publishers.py:126
 #: warehouse/manage/views/organizations.py:1805
 msgid ""
@@ -346,22 +346,22 @@ msgid ""
 "#admin-intervention for details."
 msgstr ""
 
-#: warehouse/accounts/views.py:1834
+#: warehouse/accounts/views.py:1821
 #: warehouse/manage/views/organizations.py:1828
 msgid "disabled. See https://pypi.org/help#admin-intervention for details."
 msgstr ""
 
-#: warehouse/accounts/views.py:1850
+#: warehouse/accounts/views.py:1837
 msgid ""
 "You must have a verified email in order to register a pending trusted "
 "publisher. See https://pypi.org/help#openid-connect for details."
 msgstr ""
 
-#: warehouse/accounts/views.py:1863
+#: warehouse/accounts/views.py:1850
 msgid "You can't register more than 3 pending trusted publishers at once."
 msgstr ""
 
-#: warehouse/accounts/views.py:1878
+#: warehouse/accounts/views.py:1865
 #: warehouse/manage/views/oidc_publishers.py:308
 #: warehouse/manage/views/oidc_publishers.py:423
 #: warehouse/manage/views/oidc_publishers.py:539
@@ -371,7 +371,7 @@ msgid ""
 "again later."
 msgstr ""
 
-#: warehouse/accounts/views.py:1888
+#: warehouse/accounts/views.py:1875
 #: warehouse/manage/views/oidc_publishers.py:321
 #: warehouse/manage/views/oidc_publishers.py:436
 #: warehouse/manage/views/oidc_publishers.py:552
@@ -380,23 +380,23 @@ msgstr ""
 msgid "The trusted publisher could not be registered"
 msgstr ""
 
-#: warehouse/accounts/views.py:1903
+#: warehouse/accounts/views.py:1890
 msgid ""
 "This trusted publisher has already been registered. Please contact PyPI's"
 " admins if this wasn't intentional."
 msgstr ""
 
-#: warehouse/accounts/views.py:1937
+#: warehouse/accounts/views.py:1924
 #: warehouse/manage/views/organizations.py:1893
 msgid "Registered a new pending publisher to create "
 msgstr ""
 
-#: warehouse/accounts/views.py:2080 warehouse/accounts/views.py:2093
-#: warehouse/accounts/views.py:2100
+#: warehouse/accounts/views.py:2067 warehouse/accounts/views.py:2080
+#: warehouse/accounts/views.py:2087
 msgid "Invalid publisher ID"
 msgstr ""
 
-#: warehouse/accounts/views.py:2107
+#: warehouse/accounts/views.py:2094
 msgid "Removed trusted publisher for project "
 msgstr ""
 
diff --git a/warehouse/templates/accounts/unrecognized-device.html b/warehouse/templates/accounts/unrecognized-device.html
index 1bc6085b037e..f28b84caa3fc 100644
--- a/warehouse/templates/accounts/unrecognized-device.html
+++ b/warehouse/templates/accounts/unrecognized-device.html
@@ -4,8 +4,10 @@
 {% block content %}
   <div class="horizontal-section">
     <div class="site-container">
-      <h1 class="page-title">Unrecognized device</h1>
-      <p>We did not recognize this device. Please check your email for a login confirmation link.</p>
+      <h1 class="page-title">Please confirm this login</h1>
+      <p>
+        We noticed you are attempting to log in from a new or previously unrecognized device. To ensure this is you, please check your email for a login confirmation link.
+      </p>
       <p>
         You should have received an email from <strong>noreply@pypi.org</strong> with the subject line "<strong>Unrecognized login to your PyPI account</strong>".
       </p>
diff --git a/warehouse/templates/email/unrecognized-login/body.html b/warehouse/templates/email/unrecognized-login/body.html
index fee92e786e10..ae183c0e044d 100644
--- a/warehouse/templates/email/unrecognized-login/body.html
+++ b/warehouse/templates/email/unrecognized-login/body.html
@@ -2,7 +2,7 @@
 {% extends "email/_base/body.html" %}
 {% block content %}
   <p>A login attempt was made from an unrecognized device.</p>
-  <p>To complete your login, please visit the following link:</p>
+  <p>To complete your login, please visit the following link from the same device from which you attempted to log in:</p>
   {% set link = request.route_url('accounts.confirm-login', _query={'token': token}) %}
   <p>
     <a href="{{ link }}">{{ link }}</a>
diff --git a/warehouse/templates/email/unrecognized-login/body.txt b/warehouse/templates/email/unrecognized-login/body.txt
index 940ab266ef22..519cd9600180 100644
--- a/warehouse/templates/email/unrecognized-login/body.txt
+++ b/warehouse/templates/email/unrecognized-login/body.txt
@@ -1,7 +1,8 @@
 {# SPDX-License-Identifier: Apache-2.0 -#}
 A login attempt was made from an unrecognized device.
 
-To complete your login, please visit the following link:
+To complete your login, please visit the following link from the same device
+from which you attempted to log in:
 
 {{ request.route_url('accounts.confirm-login', _query={'token': token}) }}