diff --git a/lms/djangoapps/courseware/views/views.py b/lms/djangoapps/courseware/views/views.py
index 01c79bc316..e0fdd3be6c 100644
--- a/lms/djangoapps/courseware/views/views.py
+++ b/lms/djangoapps/courseware/views/views.py
@@ -1043,6 +1043,8 @@ def dates(request, course_id):
     Display the course's dates.html, or 404 if there is no such course.
     Assumes the course_id is in a valid format.
     """
+    from lms.urls import COURSE_DATES_NAME, RESET_COURSE_DEADLINES_NAME
+
     course_key = CourseKey.from_string(course_id)
 
     # Enable NR tracing for this view based on course
@@ -1076,6 +1078,10 @@ def dates(request, course_id):
     user_timezone = user_timezone_locale['user_timezone']
     user_language = user_timezone_locale['user_language']
 
+    display_reset_dates_text = False
+    if RELATIVE_DATES_FLAG.is_enabled(course.id):
+        display_reset_dates_text = reset_deadlines_banner_should_display(course_key, request)
+
     context = {
         'course': course,
         'course_date_blocks': course_date_blocks,
@@ -1086,6 +1092,10 @@ def dates(request, course_id):
         'supports_preview_menu': True,
         'can_masquerade': can_masquerade,
         'masquerade': masquerade,
+        'display_reset_dates_text': display_reset_dates_text,
+        'reset_deadlines_url': reverse(RESET_COURSE_DEADLINES_NAME),
+        'reset_deadlines_redirect_url_base': COURSE_DATES_NAME,
+        'reset_deadlines_redirect_url_id_dict': {'course_id': str(course.id)}
     }
 
     return render_to_response('courseware/dates.html', context)
diff --git a/lms/static/sass/course/_dates.scss b/lms/static/sass/course/_dates.scss
index 653384c18e..743bcd18ac 100644
--- a/lms/static/sass/course/_dates.scss
+++ b/lms/static/sass/course/_dates.scss
@@ -18,7 +18,7 @@
     padding: 24px;
     display: flex;
     flex-wrap: wrap;
-    gap: 24px;
+    justify-content: space-between;
     max-width: $text-width-readability-max;
 
     .upgrade-banner-text {
@@ -26,6 +26,7 @@
       line-height: 24px;
       color: #414141;
       flex: 1 1 20em;
+      max-width: 70%;
     }
 
     .upgrade-button {
diff --git a/lms/templates/courseware/dates.html b/lms/templates/courseware/dates.html
index 8c7e9f5856..127e2a147d 100644
--- a/lms/templates/courseware/dates.html
+++ b/lms/templates/courseware/dates.html
@@ -30,19 +30,43 @@ from openedx.core.djangolib.markup import HTML, Text
                 % if has_locked_assignments and verified_upgrade_link:
                     <div class="upgrade-banner">
                         <div class="upgrade-banner-text">
-                            <strong>${_('You are auditing this course.')}</strong>
-                            ${_('This means that you are unable to participate in graded assignments.')}
-                            ${_('To complete graded assignments as part of this course, you can upgrade today.')}
+                            <strong>${_('You are auditing this course,')}</strong>
+                            ${_(' which means that you are unable to participate in graded assignments.')}
+                            % if display_reset_dates_text:
+                                ${_(' It looks like you missed some important deadlines based on our suggested schedule. To complete graded assignments as part of this course and shift the past due assignments into the future, you can upgrade today.')}
+                            % else:
+                                ${_(' To complete graded assignments as part of this course, you can upgrade today.')}
+                            % endif
                         </div>
                         <div class="upgrade-button">
                             <a href="${verified_upgrade_link}">
                                 <button type="button">
-                                    ${_('Upgrade now')}
+                                    % if display_reset_dates_text:
+                                        ${_('Upgrade to shift due dates')}
+                                    % else:
+                                        ${_('Upgrade now')}
+                                    % endif
                                 </button>
                             </a>
                         </div>
                     </div>
                 % endif
+                % if display_reset_dates_text and learner_is_verified:
+                    <div class="upgrade-banner">
+                        <div class="upgrade-banner-text">
+                            <strong>${_('It looks like you missed some important deadlines based on our suggested schedule.')}</strong>
+                            ${_('To keep yourself on track, you can update this schedule and shift the past due assignments into the future. Don’t worry—you won’t lose any of the progress you’ve made when you shift your due dates. ')}
+                        </div>
+                        <div class="upgrade-button">
+                            <form method="post" action="${reset_deadlines_url}">
+                                <input type="hidden" id="csrf_token" name="csrfmiddlewaretoken" value="${csrf_token}">
+                                <input type="hidden" name="reset_deadlines_redirect_url_base" value="${reset_deadlines_redirect_url_base}">
+                                <input type="hidden" name="reset_deadlines_redirect_url_id_dict" value="${reset_deadlines_redirect_url_id_dict}">
+                                <button class="upgrade-button">${_("Reset my deadlines")}</button>
+                            </form>
+                        </div>
+                    </div>
+                % endif
 
                 <% due_next_set = False %>
                 % for block in course_date_blocks:
diff --git a/lms/urls.py b/lms/urls.py
index 29e961942e..6e6c1943a7 100644
--- a/lms/urls.py
+++ b/lms/urls.py
@@ -57,6 +57,7 @@ from util import views as util_views
 
 RESET_COURSE_DEADLINES_NAME = 'reset_course_deadlines'
 RENDER_XBLOCK_NAME = 'render_xblock'
+COURSE_DATES_NAME = 'dates'
 
 if settings.DEBUG or settings.FEATURES.get('ENABLE_DJANGO_ADMIN_SITE'):
     django_autodiscover()
@@ -486,7 +487,7 @@ urlpatterns += [
             settings.COURSE_ID_PATTERN,
         ),
         courseware_views.dates,
-        name='dates',
+        name=COURSE_DATES_NAME,
     ),
 
     # Takes optional student_id for instructor use--shows profile as that student sees it.
diff --git a/openedx/features/course_experience/utils.py b/openedx/features/course_experience/utils.py
index 46ae05fbf2..a7ab4f386e 100644
--- a/openedx/features/course_experience/utils.py
+++ b/openedx/features/course_experience/utils.py
@@ -6,6 +6,7 @@ Common utilities for the course experience, including course outline.
 from datetime import timedelta
 
 from completion.models import BlockCompletion
+from django.db.models import Q
 from django.utils import timezone
 from opaque_keys.edx.keys import CourseKey
 from six.moves import range
@@ -266,9 +267,11 @@ def reset_deadlines_banner_should_display(course_key, request):
         request.user and course_overview and has_access(request.user, 'staff', course_overview, course_overview.id)
     )
     if is_self_paced and (not is_course_staff) and (not course_end_date or timezone.now() < course_end_date):
-        if (CourseEnrollment.objects.filter(
-            course=course_overview, user=request.user, mode=CourseMode.VERIFIED
-        ).exists()):
+        if CourseEnrollment.objects.filter(
+            course=course_overview, user=request.user,
+        ).filter(
+            Q(mode=CourseMode.AUDIT) | Q(mode=CourseMode.VERIFIED)
+        ).exists():
             course_block_tree = get_course_outline_block_tree(
                 request, str(course_key), request.user
             )