diff --git a/CHANGELOG.md b/CHANGELOG.md
index c0bec1526..df5828bc6 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -15,6 +15,8 @@ Changelog](https://keepachangelog.com/en/1.0.0/).
 - "Communicate as Backdoor User" PBA's HTTP requests to request headers only and
   include a timeout. #1577
 - The setup procedure for custom server_config.json files to be simpler. #1576
+- The order and content of Monkey Island's initialization logging to give
+  clearer instructions to the user and avoid confusion. #1684
 
 ### Removed
 - The VSFTPD exploiter. #1533
diff --git a/monkey/monkey_island/cc/server_setup.py b/monkey/monkey_island/cc/server_setup.py
index a3c0cf750..a99be1a40 100644
--- a/monkey/monkey_island/cc/server_setup.py
+++ b/monkey/monkey_island/cc/server_setup.py
@@ -167,11 +167,17 @@ def _start_bootloader_server() -> Thread:
 
 
 def _log_init_info():
+    MonkeyDownload.log_executable_hashes()
+
     logger.info("Monkey Island Server is running!")
     logger.info(f"version: {get_version()}")
+
+    _log_web_interface_access_urls()
+
+
+def _log_web_interface_access_urls():
+    web_interface_urls = ", ".join([f"https://{ip}:{ISLAND_PORT}" for ip in local_ip_addresses()])
     logger.info(
-        "Listening on the following URLs: {}".format(
-            ", ".join(["https://{}:{}".format(x, ISLAND_PORT) for x in local_ip_addresses()])
-        )
+        "To access the web interface, navigate to one of the the following URLs using your "
+        f"browser: {web_interface_urls}"
     )
-    MonkeyDownload.log_executable_hashes()