diff --git a/ansible/roles/cronjobs/tasks/main.yml b/ansible/roles/cronjobs/tasks/main.yml
index d11ccd1..61205d1 100644
--- a/ansible/roles/cronjobs/tasks/main.yml
+++ b/ansible/roles/cronjobs/tasks/main.yml
@@ -35,10 +35,13 @@
     hour: 0
     minute: 10
 
+# Also reloads gunicorn if CSS updated, to update the cache-busting strings
 - name: Add cronjob for generating site-icons CSS file
   cron:
     name: generate_site_icons_css
-    job: "{{ bin_dir }}/python -c \"from scripts.generate_site_icons_css import generate_css; generate_css()\""
+    job: >
+      {{ bin_dir }}/python -c "from scripts.generate_site_icons_css import generate_css; generated = generate_css(); exit(0 if generated else 1)"
+      && sudo systemctl reload gunicorn.service
     user: "{{ app_username }}"
     minute: "*/5"
 
diff --git a/ansible/roles/gunicorn/files/gunicorn_reloader.path b/ansible/roles/gunicorn/files/gunicorn_reloader.path
deleted file mode 100644
index 3fb2132..0000000
--- a/ansible/roles/gunicorn/files/gunicorn_reloader.path
+++ /dev/null
@@ -1,5 +0,0 @@
-[Path]
-PathChanged=/opt/tildes/static/css/site-icons.css
-
-[Install]
-WantedBy=multi-user.target
diff --git a/ansible/roles/gunicorn/files/gunicorn_reloader.service b/ansible/roles/gunicorn/files/gunicorn_reloader.service
deleted file mode 100644
index 21f609c..0000000
--- a/ansible/roles/gunicorn/files/gunicorn_reloader.service
+++ /dev/null
@@ -1,10 +0,0 @@
-[Unit]
-Description=gunicorn reloader
-After=network.target
-
-[Service]
-Type=oneshot
-ExecStart=/bin/systemctl reload gunicorn.service
-
-[Install]
-WantedBy=multi-user.target
diff --git a/ansible/roles/gunicorn/tasks/main.yml b/ansible/roles/gunicorn/tasks/main.yml
index cc3f268..0378da4 100644
--- a/ansible/roles/gunicorn/tasks/main.yml
+++ b/ansible/roles/gunicorn/tasks/main.yml
@@ -29,35 +29,8 @@
     state: started
     enabled: true
 
-# Set up the gunicorn_reloader service, which reloads gunicorn whenever certain files
-# are changed (such as static files, to update the cache-busting strings)
-- name: Create gunicorn_reloader service file
-  copy:
-    src: gunicorn_reloader.service
-    dest: /etc/systemd/system/gunicorn_reloader.service
-    owner: root
-    group: root
-    mode: 0644
-
-- name: Create gunicorn_reloader path-monitoring file
-  copy:
-    src: gunicorn_reloader.path
-    dest: /etc/systemd/system/gunicorn_reloader.path
-    owner: root
-    group: root
-    mode: 0644
-
-- name: Start and enable gunicorn_reloader path-monitoring service, with fallback
-  block:
-  - name: Start and enable gunicorn_reloader path-monitoring service
-    systemd_service:
-      name: gunicorn_reloader.path
-      state: started
-      enabled: true
-  rescue:
-  # Likely Docker; systemctl3.py doesn't support .path, so enable .service here
-  - name: Start and enable gunicorn.service (if .path service fails)
-    systemd_service:
-      name: gunicorn.service
-      state: started
-      enabled: true
+- name: Start and enable gunicorn service
+  systemd_service:
+    name: gunicorn.service
+    state: started
+    enabled: true
diff --git a/tildes/scripts/generate_site_icons_css.py b/tildes/scripts/generate_site_icons_css.py
index e26d99a..45d5292 100644
--- a/tildes/scripts/generate_site_icons_css.py
+++ b/tildes/scripts/generate_site_icons_css.py
@@ -34,10 +34,13 @@ def _is_output_file_outdated() -> bool:
     return False
 
 
-def generate_css() -> None:
-    """Generate the CSS file for site icons and replace the old one."""
+def generate_css() -> bool:
+    """Generate the CSS file for site icons and replace the old one.
+
+    Return True if generated, otherwise return False if skipped.
+    """
     if not _is_output_file_outdated():
-        return
+        return False
 
     with NamedTemporaryFile(mode="w") as temp_file:
         for filename in os.listdir(ICON_FOLDER):
@@ -54,3 +57,5 @@ def generate_css() -> None:
 
     # set file permissions to 644 (rw-r--r--)
     os.chmod(OUTPUT_FILE, stat.S_IRUSR | stat.S_IWUSR | stat.S_IRGRP | stat.S_IROTH)
+
+    return True