diff --git a/CMakeLists.txt b/CMakeLists.txt
index f30d8e9..bfcf04b 100644
--- a/CMakeLists.txt
+++ b/CMakeLists.txt
@@ -7,7 +7,8 @@ add_executable(${exe_name}
 	main.c
 	prompt.c
 	friendlist.c
-	chat.c)
+	chat.c
+	configdir.c)
 
 target_link_libraries(${exe_name}
 	curses)
diff --git a/configdir.c b/configdir.c
index c9f7de8..7d11d02 100644
--- a/configdir.c
+++ b/configdir.c
@@ -21,71 +21,126 @@
 #include <string.h>
 #include <stdlib.h>
 #include <stdio.h>
+#include <sys/types.h>
+#include <sys/stat.h>
+#include <errno.h>
 
-#ifdef _win32
+#ifdef WIN32
 #include <shlobj.h>
+#include <direct.h>
 #endif
 
 #ifdef __APPLE__
-#include <sys/types.h>
 #include <unistd.h>
 #include <pwd.h>
 #endif
 
+#include "configdir.h"
+
+/*
+ * Retrieves a correct configuration directory, depending on the OS used, with a trailing slash
+ */
 char *get_user_config_dir(void)
 {
-	char *user_config_dir;
+  char *user_config_dir;
 
-	#ifdef _win32
+  #ifdef WIN32
 
-	char appdata[MAX_PATH];
-	HRESULT result = SHGetFolderPath(
-		NULL,
-		CSIDL_APPDATA, // TODO: Maybe use CSIDL_LOCAL_APPDATA instead? Not sure.
-		NULL,
-		SHGFP_TYPE_CURRENT,
-		appdata
-	)
-	if (!result) return NULL;
+  char appdata[MAX_PATH];
+  HRESULT result = SHGetFolderPath(
+    NULL,
+    CSIDL_APPDATA,
+    NULL,
+    SHGFP_TYPE_CURRENT,
+    appdata
+  )
+  if (!result) return NULL;
 
-	user_config_dir = malloc(strlen(appdata) + strlen(CONFIGDIR) + 1);
-	if (user_config_dir) {
-		strcpy(user_config_dir, appdata);
-		strcat(user_config_dir, CONFIGDIR);
-	}
-	return user_config_dir;
+  user_config_dir = malloc(strlen(appdata) + 1);
+  if (user_config_dir) {
+    strcpy(user_config_dir, appdata);
+  }
+  return user_config_dir;
 
-	#elif defined __APPLE__
+  #elif defined __APPLE__
 
-	struct passwd *pass = getpwuid(getuid());
-	if (!pass) return NULL;
-	char *home = pass->pw_dir;
-	user_config_dir = malloc(strlen(home) + strlen("/Library/Application Support") + strlen(CONFIGDIR) + 1);
-	
-	if(user_config_dir) {
-		strcpy(user_config_dir, home);
-		strcat(user_config_dir, "/Library/Application Support");
-		strcat(user_config_dir, CONFIGDIR);
-	}
-	return user_config_dir;
+  struct passwd *pass = getpwuid(getuid());
+  if (!pass) return NULL;
+  char *home = pass->pw_dir;
+  user_config_dir = malloc(strlen(home) + strlen("/Library/Application Support") + 1);
+  
+  if(user_config_dir) {
+    strcpy(user_config_dir, home);
+    strcat(user_config_dir, "/Library/Application Support");
+  }
+  return user_config_dir;
 
-	#else
+  #else
 
-	if (getenv("XDG_CONFIG_HOME")) {
-		user_config_dir = malloc(strlen(getenv("XDG_CONFIG_HOME")) + strlen(CONFIGDIR) + 1);
-		if (user_config_dir) {
-			strcpy(user_config_dir, getenv("XDG_CONFIG_HOME"));
-			strcat(user_config_dir, CONFIGDIR);
-		}
-	} else {
-		user_config_dir = malloc(strlen(getenv("HOME")) + strlen("/.config") + strlen(CONFIGDIR) + 1);
-		if (user_config_dir) {
-			strcpy(user_config_dir, getenv("HOME"));
-			strcat(user_config_dir, "/.config");
-			strcat(user_config_dir, CONFIGDIR);
-		}
-	}
-	return user_config_dir;
+  if (getenv("XDG_CONFIG_HOME")) {
+    user_config_dir = malloc(strlen(getenv("XDG_CONFIG_HOME")) + 1);
+    if (user_config_dir) {
+      strcpy(user_config_dir, getenv("XDG_CONFIG_HOME"));
+    }
+  } else {
+    user_config_dir = malloc(strlen(getenv("HOME")) + strlen("/.config") + 1);
+    if (user_config_dir) {
+      strcpy(user_config_dir, getenv("HOME"));
+      strcat(user_config_dir, "/.config");
+    }
+  }
+  return user_config_dir;
 
-	#endif
+  #endif
+}
+
+/*
+ * Creates the config directory.
+ */
+int create_user_config_dir(char *path)
+{ 
+
+  int mkdir_err;
+
+  #ifdef WIN32
+
+  char *fullpath = malloc(strlen(path) + strlen(CONFIGDIR) + 1);
+  strcpy(fullpath, path);
+  strcat(fullpath, CONFIGDIR);
+
+  mkdir_err = _mkdir(fullpath);
+
+  if (mkdir_err) {
+    if(errno != EEXIST) return -1;
+    struct _stat buf;
+    if(_wstat64(fullpath, &buf)) return -1;
+    if(!S_ISDIR(buf.st_mode)) return -1;
+  }
+
+  #else
+
+  mkdir_err = mkdir(path, 0700);
+  struct stat buf;
+
+  if(mkdir_err) {
+    if(errno != EEXIST) return -1;
+    if(stat(path, &buf)) return -1;
+    if(!S_ISDIR(buf.st_mode)) return -1;
+  }
+
+  char *fullpath = malloc(strlen(path) + strlen(CONFIGDIR) + 1);
+  strcpy(fullpath, path);
+  strcat(fullpath, CONFIGDIR);
+
+  mkdir_err = mkdir(fullpath, 0700);
+
+  if(mkdir_err) {
+    if(errno != EEXIST) return -1;
+    if(stat(fullpath, &buf)) return -1;
+    if(!S_ISDIR(buf.st_mode)) return -1;
+  }
+  
+  #endif
+
+  return 0;
 }
\ No newline at end of file
diff --git a/configdir.h b/configdir.h
index 441ffda..d9837d7 100644
--- a/configdir.h
+++ b/configdir.h
@@ -23,5 +23,11 @@
 #else
 #define CONFIGDIR "/toxic/"
 #endif
+ 
+#ifndef S_ISDIR
+#define S_ISDIR(mode)  (((mode) & S_IFMT) == S_IFDIR)
+#endif
 
-char *get_user_config_dir(void);
\ No newline at end of file
+char *get_user_config_dir(void);
+
+int create_user_config_dir(char *path);
\ No newline at end of file
diff --git a/main.c b/main.c
index ec439c8..cb0d9e1 100644
--- a/main.c
+++ b/main.c
@@ -3,11 +3,19 @@
  */
 
 #include <curses.h>
+#include <errno.h>
 #include <stdio.h>
 #include <stdlib.h>
 #include <stdbool.h>
 #include <stdint.h>
 
+#ifdef _win32
+#include <direct.h>
+#else
+#include <sys/stat.h>
+#include <sys/types.h>
+#endif
+
 #include "../../core/Messenger.h"
 #include "../../core/network.h"
 
@@ -332,26 +340,19 @@ int main(int argc, char *argv[])
 {
   int ch;
   int f_flag = 0;
-  char *configdir = get_user_config_dir();
-  char *default_file = "data";
-  int mkdir_err
-  #ifdef _win32
-  mkdir_err = _mkdir(configdir);
-  #else
-  mkdir_err = mkdir(configdir, 0700);
-  #endif
-
+  char *user_config_dir = get_user_config_dir();
   char *filename;
-  if(mkdir_err == -1) {
-    filename = default_file;
+  int config_err = create_user_config_dir(user_config_dir);
+  if(config_err) {
+    filename = "data";
   } else {
-    filename = malloc(strlen(configdir) + strlen(default_file) + 1);
-    strcpy(filename, configdir);
-    strcat(filename, default_file);
+    filename = malloc(strlen(user_config_dir) + strlen(CONFIGDIR) + strlen("data") + 1);
+    strcpy(filename, user_config_dir);
+    strcat(filename, CONFIGDIR);
+    strcat(filename, "data");
   }
   
   ToxWindow* a;
-
   int i = 0;
   for (i = 0; i < argc; ++i) {
     if (argv[i] == NULL)
@@ -378,6 +379,13 @@ int main(int argc, char *argv[])
                             "defaulting to 'data' for a keyfile...\n");
     attroff(COLOR_PAIR(3) | A_BOLD);
   }
+
+  if(config_err) {
+    attron(COLOR_PAIR(3) | A_BOLD);
+    wprintw(prompt->window, "Unable to determine configuration directory!\n"
+                            "defaulting to 'data' for a keyfile...\n");
+    attroff(COLOR_PAIR(3) | A_BOLD);
+  }
   
   while(true) {
     /* Update tox */