diff --git a/src/proxy/tinymitm/proxy.cpp b/src/proxy/tinymitm/proxy.cpp
index b334c90..18c9a6f 100644
--- a/src/proxy/tinymitm/proxy.cpp
+++ b/src/proxy/tinymitm/proxy.cpp
@@ -126,16 +126,35 @@ bool TinyMITMProxy::init()
 {
     _running = true;
 
-    // wolfssl setup
-    if (wolfSSL_Init() != WOLFSSL_SUCCESS) return false;
+    TINYMITM_WRITELOG(info, "proxy init");
 
+    TINYMITM_WRITELOG(verbose, "wolfssl init");
+
+    // wolfssl setup
+    if (wolfSSL_Init() != WOLFSSL_SUCCESS)
+    {
+        TINYMITM_WRITELOG(error, "wolfssl failed to initialize");
+        return false;
+    }
+    TINYMITM_WRITELOG(verbose, "wolfssl context creation");
     _clientCtx = wolfSSL_CTX_new(wolfTLSv1_3_client_method());
-    if (!_clientCtx) return false;
+    if (!_clientCtx)
+    {
+        TINYMITM_WRITELOG(error, "failed to create wolfssl context");
+        return false;
+    }
 
     wolfSSL_CTX_set_verify(_clientCtx, WOLFSSL_VERIFY_NONE, nullptr);
 
     // cert setup
-    if (!_certManager.init()) return false;
+    TINYMITM_WRITELOG(verbose, "certmanager init");
+    if (!_certManager.init())
+    {
+        TINYMITM_WRITELOG(error, "certmanager failed to initialize");
+        return false;
+    }
+
+    TINYMITM_WRITELOG(verbose, "loading / generating CA");
     bool hasCA = false;
     if (_config.autoGenerateCA)
     {
@@ -148,28 +167,51 @@ bool TinyMITMProxy::init()
     else
         hasCA = _certManager.loadCA(_config.customCaCertDer.c_str(), _config.customCaKeyDer.c_str());
 
-    if (!hasCA) return false;
+    if (!hasCA)
+    {
+        TINYMITM_WRITELOG(error, "certManager was unable to obtain a certificate");
+        return false;
+    }
 
 #ifdef _WIN32
-    if (_config.installToSystemStore) _certManager.installCertificate();
+    TINYMITM_WRITELOG(verbose, "installing CA");
+    if (_config.installToSystemStore)
+    {
+        if (!_certManager.installCertificate())
+        {
+            TINYMITM_WRITELOG(error, "failed to install CA");
+            return false;
+        }
+    }
 #endif
 
     // socket setup
 #ifdef _WIN32
+    TINYMITM_WRITELOG(verbose, "starting winsock");
     WSADATA wsaData;
-    if (WSAStartup(MAKEWORD(2, 2), &wsaData) != 0) return false;
+    if (WSAStartup(MAKEWORD(2, 2), &wsaData) != 0)
+    {
+        TINYMITM_WRITELOG(error, "failed to start winsock");
+        return false;
+    }
 #endif
 
+    TINYMITM_WRITELOG(verbose, "setting up listen socket");
     _listenSocket = socket(AF_INET, SOCK_STREAM, 0);
     sockaddr_in addr{};
     addr.sin_family = AF_INET;
     addr.sin_port = htons(_config.port);
     addr.sin_addr.s_addr = INADDR_ANY;
 
-    if (bind(_listenSocket, (sockaddr*)&addr, sizeof(addr)) == SOCKET_ERROR) return false;
+    if (bind(_listenSocket, (sockaddr*)&addr, sizeof(addr)) == SOCKET_ERROR)
+    {
+        TINYMITM_WRITELOG(error, "failed to bind listensocket");
+        return false;
+    }
     listen(_listenSocket, SOMAXCONN);
 
     // handler threads
+    TINYMITM_WRITELOG(verbose, "starting handler threads");
     for (unsigned char i = 0; i < _config.threadCount; i++)
     {
         _poolThreads.emplace_back([this]() {
@@ -187,6 +229,7 @@ bool TinyMITMProxy::init()
     }
 
     // dispatcher thread
+    TINYMITM_WRITELOG(verbose, "starting handler thread");
     _dispatchThread = std::thread([this] {
         while (_running)
         {
@@ -200,6 +243,8 @@ bool TinyMITMProxy::init()
         }
     });
 
+    TINYMITM_WRITELOG(info, "proxy started successfully");
+
     return true;
 }