diff --git a/generic/templates/generic/trainees_bulk_update.html b/generic/templates/generic/trainees_bulk_update.html
index b43fdf36..109a97d0 100644
--- a/generic/templates/generic/trainees_bulk_update.html
+++ b/generic/templates/generic/trainees_bulk_update.html
@@ -1,50 +1,50 @@
 {% extends 'generic/base.html' %}
 
 {% block content %}
-<h2>Bulk update trainees (paste spreadsheet text)</h2>
+    <h2>Bulk update trainees (paste spreadsheet text)</h2>
 
-<p>Paste the spreadsheet rows below. Headings like "Year 1 - Group 1" are used to set the grade (Year N -> STN). Rows should contain "Name <tab or 2+spaces> Supervisor".</p>
+    <p>Paste the spreadsheet rows below. Headings like "Year 1 - Group 1" are used to set the grade (Year N -> STN). Rows should contain "Name <tab or 2+spaces> Supervisor".</p>
 
-<form method="post">
-    {% csrf_token %}
-    <textarea name="data" rows="18" style="width:100%">{% if request.POST.data %}{{ request.POST.data }}{% endif %}</textarea>
-    <div style="margin-top:8px">
-        <button type="submit" name="action" value="preview" class="btn btn-primary">Preview</button>
-        <button type="submit" name="action" value="apply" class="btn btn-danger" onclick="return confirm('This will apply updates to matched trainee profiles. Are you sure?')">Apply updates</button>
-    </div>
-</form>
+        <form method="post">
+            {% csrf_token %}
+            <textarea name="data" rows="18" style="width:100%">{% if request.POST.data %}{{ request.POST.data }}{% endif %}</textarea>
+            <div style="margin-top:8px">
+                <button type="submit" name="action" value="preview" class="btn btn-primary">Preview</button>
+                <button type="submit" name="action" value="apply" class="btn btn-danger" onclick="return confirm('This will apply updates to matched trainee profiles. Are you sure?')">Apply updates</button>
+            </div>
+        </form>
 
-{% if preview %}
-    <h3>Preview ({{ preview|length }} rows)</h3>
-    <table class="table table-sm">
-        <thead>
-            <tr>
-                <th>Raw</th>
-                <th>Name</th>
-                <th>Grade</th>
-                <th>Matched user</th>
-                <th>Supervisor text</th>
-                <th>Matched supervisor</th>
-            </tr>
-        </thead>
-        <tbody>
-            {% for r in preview %}
-                <tr>
-                    <td><pre style="margin:0">{{ r.raw }}</pre></td>
-                    <td>{{ r.norm_name }}</td>
-                    <td>{{ r.grade }}</td>
-                    <td>{% if r.matched_user %}<a href="{% url 'account_profile' r.matched_user.username %}">{{ r.matched_user.first_name }} {{ r.matched_user.last_name }}</a>{% else %}<span style="color:red">No match</span>{% endif %}</td>
-                    <td>{{ r.supervisor_text }}</td>
-                    <td>{% if r.matched_supervisor %}<a href="{% url 'generic:supervisor_detail' r.matched_supervisor.pk %}">{{ r.matched_supervisor.name }}</a>{% else %}<span style="color:red">No match</span>{% endif %}</td>
-                </tr>
-            {% endfor %}
-        </tbody>
-    </table>
-{% endif %}
+        {% if preview %}
+            <h3>Preview ({{ preview|length }} rows)</h3>
+            <table class="table table-sm">
+                <thead>
+                    <tr>
+                        <th>Raw</th>
+                        <th>Name</th>
+                        <th>Grade</th>
+                        <th>Matched user</th>
+                        <th>Supervisor text</th>
+                        <th>Matched supervisor</th>
+                    </tr>
+                </thead>
+                <tbody>
+                    {% for r in preview %}
+                        <tr>
+                            <td><pre style="margin:0">{{ r.raw }}</pre></td>
+                            <td>{{ r.norm_name }}</td>
+                            <td>{{ r.grade }}</td>
+                            <td>{% if r.matched_user %}<a href="{% url 'account_profile' r.matched_user.username %}">{{ r.matched_user.first_name }} {{ r.matched_user.last_name }}</a>{% else %}<span style="color:red">No match</span>{% endif %}</td>
+                            <td>{{ r.supervisor_text }}</td>
+                            <td>{% if r.matched_supervisor %}<a href="{% url 'generic:supervisor_detail' r.matched_supervisor.pk %}">{{ r.matched_supervisor.name }}</a>{% else %}<span style="color:red">No match</span>{% endif %}</td>
+                        </tr>
+                    {% endfor %}
+                </tbody>
+            </table>
+        {% endif %}
 
-{% if report %}
-    <h3>Apply report</h3>
-    <p>Updated: {{ report.updated }}; Skipped (no user matched): {{ report.skipped }}</p>
-{% endif %}
+        {% if report %}
+            <h3>Apply report</h3>
+            <p>Updated: {{ report.updated }}; Skipped (no user matched): {{ report.skipped }}</p>
+        {% endif %}
 
 {% endblock %}
diff --git a/generic/views.py b/generic/views.py
index 389b8974..edba078d 100644
--- a/generic/views.py
+++ b/generic/views.py
@@ -4262,7 +4262,6 @@ def trainees_bulk_update_from_spreadsheet(request):
     - Preview: parse the pasted text and show rows with any matched user / supervisor
     - Apply: apply grade and supervisor updates for matched users
     """
-    logger.debug("Trainees bulk update called")
 
     import re
 
@@ -4309,11 +4308,27 @@ def trainees_bulk_update_from_spreadsheet(request):
 
             matched_user = None
             if first and last:
+                # Prefer an exact first+last match
                 qs = User.objects.filter(first_name__iexact=first, last_name__iexact=last)
-                if not qs.exists():
-                    qs = User.objects.filter(last_name__iexact=last)
                 if qs.exists():
                     matched_user = qs.first()
+                else:
+                    # Fallback: only match by last name when the last-name query returns
+                    # a single candidate AND the candidate's first name reasonably
+                    # matches the provided first token. This avoids ambiguous matches
+                    # (e.g. Maria vs Stephanie both 'Bailey'). We accept a match when
+                    # the candidate first name startswith the first 3 chars of the
+                    # provided first token, or contains it as a substring (case-ins).
+                    candidates = User.objects.filter(last_name__iexact=last)
+                    if candidates.count() == 1:
+                        candidate = candidates.first()
+                        cand_first = (candidate.first_name or "").strip()
+                        if cand_first:
+                            # take at most 3 chars for prefix comparison
+                            prefix = first[:3].lower()
+                            cand_first_low = cand_first.lower()
+                            if cand_first_low.startswith(prefix) or first.lower() in cand_first_low:
+                                matched_user = candidate
 
             matched_supervisor = None
             if supervisor_part: