diff --git a/monkey/monkey_island/cc/server_utils/island_logger.py b/monkey/monkey_island/cc/server_utils/island_logger.py
index f8eca8cbb..a512e0217 100644
--- a/monkey/monkey_island/cc/server_utils/island_logger.py
+++ b/monkey/monkey_island/cc/server_utils/island_logger.py
@@ -1,6 +1,7 @@
 import json
 import logging.config
 import os
+from typing import Dict
 
 from monkey_island.cc.consts import DEFAULT_LOGGING_CONFIG_PATH
 
@@ -28,6 +29,17 @@ def json_setup_logging(
     if os.path.exists(path):
         with open(path, "rt") as f:
             config = json.load(f)
+            _expanduser_log_file_paths(config)
             logging.config.dictConfig(config)
     else:
         logging.basicConfig(level=default_level)
+
+
+def _expanduser_log_file_paths(config: Dict):
+    handlers = config.get("handlers", {})
+
+    for handler_settings in handlers.values():
+        if "filename" in handler_settings:
+            handler_settings["filename"] = os.path.expanduser(
+                handler_settings["filename"]
+            )
diff --git a/monkey/monkey_island/cc/test_island_logger.py b/monkey/monkey_island/cc/test_island_logger.py
new file mode 100644
index 000000000..bd9de46f4
--- /dev/null
+++ b/monkey/monkey_island/cc/test_island_logger.py
@@ -0,0 +1,29 @@
+import logging
+import os
+
+from monkey_island.cc.consts import MONKEY_ISLAND_ABS_PATH
+from monkey_island.cc.island_logger import json_setup_logging
+
+TEST_LOGGING_CONFIG_PATH = os.path.join(MONKEY_ISLAND_ABS_PATH, "cc", "testing",
+                                        "logger_config.json")
+
+
+def set_home_env(monkeypatch, tmpdir):
+    monkeypatch.setenv("HOME", tmpdir)
+
+
+def test_expanduser_filename(monkeypatch, tmpdir):
+    INFO_LOG = os.path.join(tmpdir, "info.log")
+    TEST_STRING = "Hello, Monkey!"
+
+    set_home_env(monkeypatch, tmpdir)
+
+    json_setup_logging(TEST_LOGGING_CONFIG_PATH)
+
+    logger = logging.getLogger("TestLogger")
+    logger.info(TEST_STRING)
+
+    assert os.path.isfile(INFO_LOG)
+    with open(INFO_LOG, "r") as f:
+        line = f.readline()
+        assert TEST_STRING in line
diff --git a/monkey/monkey_island/cc/testing/logger_config.json b/monkey/monkey_island/cc/testing/logger_config.json
new file mode 100644
index 000000000..b3ad82641
--- /dev/null
+++ b/monkey/monkey_island/cc/testing/logger_config.json
@@ -0,0 +1,33 @@
+{
+  "version": 1,
+  "disable_existing_loggers": false,
+  "formatters": {
+    "simple": {
+      "format": "%(asctime)s - %(filename)s:%(lineno)s - %(funcName)10s() - %(levelname)s - %(message)s"
+    }
+  },
+  "handlers": {
+    "console": {
+      "class": "logging.StreamHandler",
+      "level": "DEBUG",
+      "formatter": "simple",
+      "stream": "ext://sys.stdout"
+    },
+    "info_file_handler": {
+      "class": "logging.handlers.RotatingFileHandler",
+      "level": "INFO",
+      "formatter": "simple",
+      "filename": "~/info.log",
+      "maxBytes": 10485760,
+      "backupCount": 20,
+      "encoding": "utf8"
+    }
+  },
+  "root": {
+    "level": "DEBUG",
+    "handlers": [
+      "console",
+      "info_file_handler"
+    ]
+  }
+}