diff --git a/backend/app/services/password_setup_service.py b/backend/app/services/password_setup_service.py
index 0721f11..0995942 100644
--- a/backend/app/services/password_setup_service.py
+++ b/backend/app/services/password_setup_service.py
@@ -65,7 +65,11 @@ def send_password_setup_email(db: Session, user: User) -> None:
         f"{set_password_url}\n\n"
         "This link expires in 24 hours and can only be used once."
     )
-    send_webhook_email(db, to=user.email, subject=subject, message=message, full_name=user.full_name)
+    sent = send_webhook_email(db, to=user.email, subject=subject, message=message, full_name=user.full_name)
+    if not sent:
+        raise BusinessRuleViolation(
+            "Failed to send the email — check the webhook URL/API key in Settings and the server logs."
+        )
 
 
 def _get_valid_token_or_raise(db: Session, token: str) -> PasswordSetupToken:
diff --git a/backend/app/services/webhook_email_service.py b/backend/app/services/webhook_email_service.py
index da0e40d..513e263 100644
--- a/backend/app/services/webhook_email_service.py
+++ b/backend/app/services/webhook_email_service.py
@@ -159,8 +159,9 @@ def send_webhook_email(
     """POST a notification email to the configured webhook.
 
     Best-effort: returns False (and logs a warning) if no webhook is
-    configured, *to* is empty, or the request fails — never raises, since
-    a webhook outage must not break whatever triggered the notification.
+    configured, *to* is empty, the request fails, or the webhook responds
+    with a non-2xx status — never raises, since a webhook outage must not
+    break whatever triggered the notification.
     """
     if not to:
         return False
@@ -174,12 +175,18 @@ def send_webhook_email(
     headers = {"x-api-key": api_key} if api_key else {}
 
     try:
-        requests.post(
+        response = requests.post(
             webhook_url,
             json={"to": to, "subject": subject, "body": build_email_body(full_name, message)},
             headers=headers,
             timeout=10,
         )
+        if not response.ok:
+            logger.warning(
+                "Email webhook rejected the request for %s: HTTP %d — %s",
+                to, response.status_code, response.text[:500],
+            )
+            return False
         return True
     except requests.RequestException:
         logger.warning("Email webhook call failed for %s", to, exc_info=True)
diff --git a/backend/tests/test_password_setup_flow.py b/backend/tests/test_password_setup_flow.py
index dcb51d1..3a257a3 100644
--- a/backend/tests/test_password_setup_flow.py
+++ b/backend/tests/test_password_setup_flow.py
@@ -84,6 +84,57 @@ def test_send_password_email_posts_to_webhook_and_issues_token(api, db, auth_hea
     assert token_row.used_at is None
 
 
+def test_send_password_email_fails_loudly_when_webhook_rejects(api, auth_headers, new_user_id):
+    """A webhook that's reachable but rejects the request (bad URL/API key,
+    wrong Power Automate config, etc.) must not be reported as a success —
+    previously the HTTP response status was never checked."""
+    api(
+        "patch", "/api/v1/system/email-webhook-config", auth_headers,
+        json={"url": "https://example.com/power-automate-hook"},
+    )
+
+    from unittest.mock import MagicMock
+
+    fake_response = MagicMock(ok=False, status_code=404, text="not found")
+    with patch("app.services.webhook_email_service.requests.post", return_value=fake_response):
+        resp = api("post", f"/api/v1/users/{new_user_id}/send-password-email", auth_headers)
+    assert resp.status_code == 400
+    assert "failed to send" in resp.text.lower()
+
+
+def test_send_password_email_resend_after_password_set_is_a_reset_email(api, db, auth_headers, new_user_id):
+    """Once a user has already set their password, hitting 'Send Email'
+    again must still actually send — as a password-reset email — not
+    silently no-op."""
+    api(
+        "patch", "/api/v1/system/email-webhook-config", auth_headers,
+        json={"url": "https://example.com/power-automate-hook"},
+    )
+
+    with patch("app.services.webhook_email_service.requests.post") as mock_post:
+        resp = api("post", f"/api/v1/users/{new_user_id}/send-password-email", auth_headers)
+    assert resp.status_code == 200, resp.text
+    first_payload = mock_post.call_args.kwargs["json"]
+    assert first_payload["subject"] == "Set Your Password"
+
+    from app.models.password_setup_token import PasswordSetupToken
+    token_row = db.query(PasswordSetupToken).filter(
+        PasswordSetupToken.user_id == uuid.UUID(new_user_id),
+    ).first()
+    api(
+        "post", "/api/v1/auth/set-password", {},
+        json={"token": token_row.token, "new_password": "BrandNewPass123!@#"},
+    )
+
+    # Now the user has must_change_password=False — resending must still
+    # go through, this time as a reset email.
+    with patch("app.services.webhook_email_service.requests.post") as mock_post_2:
+        resp2 = api("post", f"/api/v1/users/{new_user_id}/send-password-email", auth_headers)
+    assert resp2.status_code == 200, resp2.text
+    mock_post_2.assert_called_once()
+    second_payload = mock_post_2.call_args.kwargs["json"]
+    assert second_payload["subject"] == "Reset Your Password"
+
 def test_set_password_with_valid_token_succeeds(api, db, auth_headers, new_user_id):
     api(
         "patch", "/api/v1/system/email-webhook-config", auth_headers,