diff --git a/src/bootstrap.c b/src/bootstrap.c
index 2058c9734..c0d062170 100644
--- a/src/bootstrap.c
+++ b/src/bootstrap.c
@@ -36,6 +36,7 @@
 #include "line_info.h"
 #include "misc_tools.h"
 #include "prompt.h"
+#include "run_options.h"
 #include "settings.h"
 #include "windows.h"
 
diff --git a/src/misc_tools.c b/src/misc_tools.c
index 2ae2bf0a9..c61e2f80f 100644
--- a/src/misc_tools.c
+++ b/src/misc_tools.c
@@ -559,7 +559,7 @@ size_t copy_tox_str(char *msg, size_t size, const char *data, size_t length)
    returns length of s if char not found or 0 if s is NULL. */
 int char_find(int idx, const char *s, char ch)
 {
-    if (!s) {
+    if (s == NULL) {
         return 0;
     }
 
@@ -578,7 +578,7 @@ int char_find(int idx, const char *s, char ch)
    returns 0 if char not found or s is NULL (skips 0th index). */
 int char_rfind(const char *s, char ch, int len)
 {
-    if (!s) {
+    if (s == NULL) {
         return 0;
     }
 
diff --git a/src/name_lookup.c b/src/name_lookup.c
index fb0beff4c..c1b696af5 100644
--- a/src/name_lookup.c
+++ b/src/name_lookup.c
@@ -30,6 +30,7 @@
 #include "global_commands.h"
 #include "line_info.h"
 #include "misc_tools.h"
+#include "run_options.h"
 #include "toxic.h"
 #include "windows.h"
 
diff --git a/src/run_options.h b/src/run_options.h
new file mode 100644
index 000000000..07bb2dae1
--- /dev/null
+++ b/src/run_options.h
@@ -0,0 +1,57 @@
+/*  run_options.h
+ *
+ *
+ *  Copyright (C) 2024 Toxic All Rights Reserved.
+ *
+ *  This file is part of Toxic.
+ *
+ *  Toxic is free software: you can redistribute it and/or modify
+ *  it under the terms of the GNU General Public License as published by
+ *  the Free Software Foundation, either version 3 of the License, or
+ *  (at your option) any later version.
+ *
+ *  Toxic is distributed in the hope that it will be useful,
+ *  but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *  MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ *  GNU General Public License for more details.
+ *
+ *  You should have received a copy of the GNU General Public License
+ *  along with Toxic.  If not, see <http://www.gnu.org/licenses/>.
+ *
+ */
+
+#ifndef RUN_OPTIONS_H
+
+#include <stdbool.h>
+#include <stdio.h>  // needed for FILE
+#include <stdint.h>
+
+#include "toxic_constants.h"
+
+typedef struct Run_Options {
+    bool use_ipv4;
+    bool force_tcp;
+    bool disable_local_discovery;
+    bool debug;
+    bool default_locale;
+    bool use_custom_data;
+    bool use_custom_config_file;
+    bool no_connect;
+    bool encrypt_data;
+    bool unencrypt_data;
+
+    char nameserver_path[MAX_STR_SIZE];
+    char config_path[MAX_STR_SIZE];
+    char nodes_path[MAX_STR_SIZE];
+
+    bool logging;
+    FILE *log_fp;
+
+    char proxy_address[256];
+    uint8_t proxy_type;
+    uint16_t proxy_port;
+
+    uint16_t tcp_port;
+} Run_Options;
+
+#endif /* RUN_OPTIONS_H */
diff --git a/src/settings.c b/src/settings.c
index a087c5126..b3feff0b2 100644
--- a/src/settings.c
+++ b/src/settings.c
@@ -31,6 +31,7 @@
 #include "groupchats.h"
 #include "misc_tools.h"
 #include "notify.h"
+#include "run_options.h"
 #include "toxic.h"
 #include "windows.h"
 
@@ -340,29 +341,50 @@ static void set_key_binding(int *key, const char **bind)
     }
 }
 
-static bool get_settings_path(char *path, unsigned int path_size, const char *patharg)
+#define TOXIC_CONF_FILE_EXT ".conf"
+
+bool settings_load_config_file(Run_Options *run_opts, const char *data_path)
 {
-    if (patharg != NULL) {
-        snprintf(path, path_size, "%s", patharg);
-        return true;
-    }
+    char tmp_path[MAX_STR_SIZE] = {0};
+
+    if (run_opts->use_custom_config_file) {
+        snprintf(tmp_path, sizeof(tmp_path), "%s", run_opts->config_path);
+    } else if (run_opts->use_custom_data) {
+        char tmp_data[MAX_STR_SIZE - strlen(TOXIC_CONF_FILE_EXT)];
+
+        if (strlen(data_path) >= sizeof(tmp_data)) {
+            return false;
+        }
 
-    char *user_config_dir = get_user_config_dir();
-    snprintf(path, path_size, "%s%stoxic.conf", user_config_dir, CONFIGDIR);
-    free(user_config_dir);
+        snprintf(tmp_data, sizeof(tmp_data), "%s", data_path);
+
+        const int dot_idx = char_rfind(tmp_data, '.', strlen(tmp_data));
+
+        if (dot_idx > 0) {
+            tmp_data[dot_idx] = '\0';  // remove .tox file extension (or any others) if it exists
+        }
+
+        snprintf(tmp_path, sizeof(tmp_path), "%s%s", tmp_data, TOXIC_CONF_FILE_EXT);
+    } else {
+        char *user_config_dir = get_user_config_dir();
+        snprintf(tmp_path, sizeof(tmp_path), "%s%stoxic%s", user_config_dir, CONFIGDIR, TOXIC_CONF_FILE_EXT);
+        free(user_config_dir);
+    }
 
     /* make sure path exists or is created on first time running */
-    if (!file_exists(path)) {
-        FILE *fp = fopen(path, "w");
+    if (!file_exists(tmp_path)) {
+        FILE *fp = fopen(tmp_path, "w");
 
         if (fp == NULL) {
-            fprintf(stderr, "failed to open config path: %s\n", path);
+            fprintf(stderr, "failed to create config path `%s`\n", tmp_path);
             return false;
         }
 
         fclose(fp);
     }
 
+    snprintf(run_opts->config_path, sizeof(run_opts->config_path), "%s", tmp_path);
+
     return true;
 }
 
@@ -404,22 +426,17 @@ static const char *extract_setting_public_key(const config_setting_t *keys)
 /*
  * Initializes `cfg` with the contents from the toxic config file.
  *
- * `patharg` points to a user specified config path. If `patharg` is NULL
- * the default config path will be used.
- *
  * Return 0 on success.
- * Return -1 if we failed to fetch or create the config path.
+ * Return -1 if the config file was not set by the client.
  * Return -2 if the config file cannot be read or is invalid.
  */
-static int settings_init_config(config_t *cfg, const char *patharg)
+static int settings_init_config(config_t *cfg, const Run_Options *run_opts)
 {
-    char path[MAX_STR_SIZE] = {0};
-
-    if (!get_settings_path(path, sizeof(path), patharg)) {
+    if (string_is_empty(run_opts->config_path)) {
         return -1;
     }
 
-    if (!config_read_file(cfg, path)) {
+    if (!config_read_file(cfg, run_opts->config_path)) {
         fprintf(stderr, "config_read_file() error: %s:%d - %s\n", config_error_file(cfg),
                 config_error_line(cfg), config_error_text(cfg));
         return -2;
@@ -428,12 +445,12 @@ static int settings_init_config(config_t *cfg, const char *patharg)
     return 0;
 }
 
-int settings_load_conferences(const char *patharg)
+int settings_load_conferences(const Run_Options *run_opts)
 {
     config_t cfg[1];
     config_init(cfg);
 
-    const int c_ret = settings_init_config(cfg, patharg);
+    const int c_ret = settings_init_config(cfg, run_opts);
 
     if (c_ret < 0) {
         config_destroy(cfg);
@@ -480,12 +497,12 @@ int settings_load_conferences(const char *patharg)
     return 0;
 }
 
-int settings_load_groups(const char *patharg)
+int settings_load_groups(const Run_Options *run_opts)
 {
     config_t cfg[1];
     config_init(cfg);
 
-    const int c_ret = settings_init_config(cfg, patharg);
+    const int c_ret = settings_init_config(cfg, run_opts);
 
     if (c_ret < 0) {
         config_destroy(cfg);
@@ -532,12 +549,12 @@ int settings_load_groups(const char *patharg)
     return 0;
 }
 
-int settings_load_friends(const char *patharg)
+int settings_load_friends(const Run_Options *run_opts)
 {
     config_t cfg[1];
     config_init(cfg);
 
-    const int c_ret = settings_init_config(cfg, patharg);
+    const int c_ret = settings_init_config(cfg, run_opts);
 
     if (c_ret < 0) {
         config_destroy(cfg);
@@ -600,7 +617,7 @@ int settings_load_friends(const char *patharg)
     return 0;
 }
 
-int settings_load_main(Client_Config *s, const char *patharg)
+int settings_load_main(Client_Config *s, const Run_Options *run_opts)
 {
     config_t cfg[1];
     config_init(cfg);
@@ -616,7 +633,7 @@ int settings_load_main(Client_Config *s, const char *patharg)
     audio_defaults(s);
 #endif
 
-    const int c_ret = settings_init_config(cfg, patharg);
+    const int c_ret = settings_init_config(cfg, run_opts);
 
     if (c_ret < 0) {
         config_destroy(cfg);
diff --git a/src/settings.h b/src/settings.h
index 354bc8a83..7c3d82428 100644
--- a/src/settings.h
+++ b/src/settings.h
@@ -141,6 +141,27 @@ enum settings_values {
 #define LOG_TIMESTAMP_DEFAULT  "%Y/%m/%d [%H:%M:%S]"
 #define MPLEX_AWAY_NOTE "Away from keyboard, be back soon!"
 
+typedef struct Run_Options Run_Options;
+
+/*
+ * Loads the config file into `run_opts` and creates an empty file if it does not
+ * already exist. This function must be called before any other `settings_load` function.
+ *
+ * If the client has set a custom config file via the run option it will be
+ * prioritized.
+ *
+ * If the client is using the default tox data file and has not specified a custom
+ * config file, the default config file in the user config directory is used
+ *
+ * If the client is using a custom tox data file, the config path and filename will be
+ * identical to those of the data file, but with a `.conf` file extension.
+ *
+ * `data_path` is the name of the tox profile being used.
+ *
+ * Returns true if config file is successfully loaded.
+ */
+bool settings_load_config_file(Run_Options *run_opts, const char *data_path);
+
 /*
  * Loads general toxic settings from the toxic config file pointed to by `patharg'.
  *
@@ -148,7 +169,7 @@ enum settings_values {
  * Return -1 if we fail to open the file path.
  * Return -2 if libconfig fails to read the config file.
  */
-int settings_load_main(Client_Config *s, const char *patharg);
+int settings_load_main(Client_Config *s, const Run_Options *run_opts);
 
 /*
  * Loads friend config settings from the toxic config file pointed to by `patharg`.
@@ -160,7 +181,7 @@ int settings_load_main(Client_Config *s, const char *patharg);
  *
  * This function will have no effect on friends that are added in the future.
  */
-int settings_load_friends(const char *patharg);
+int settings_load_friends(const Run_Options *run_opts);
 
 /*
  * Loads groupchat config settings from the toxic config file pointed to by `patharg`.
@@ -172,7 +193,7 @@ int settings_load_friends(const char *patharg);
  *
  * This function will have no effect on groupchat instances that are created in the future.
  */
-int settings_load_groups(const char *patharg);
+int settings_load_groups(const Run_Options *run_opts);
 
 /*
  * Loads conference config settings from the toxic config file pointed to by `patharg`.
@@ -184,6 +205,6 @@ int settings_load_groups(const char *patharg);
  *
  * This function will have no effect on conference instances that are created in the future.
  */
-int settings_load_conferences(const char *patharg);
+int settings_load_conferences(const Run_Options *run_opts);
 
 #endif /* SETTINGS_H */
diff --git a/src/toxic.c b/src/toxic.c
index 0acdc7273..b4d3ee117 100644
--- a/src/toxic.c
+++ b/src/toxic.c
@@ -62,6 +62,7 @@
 #include "name_lookup.h"
 #include "notify.h"
 #include "prompt.h"
+#include "run_options.h"
 #include "settings.h"
 #include "term_mplex.h"
 #include "toxic.h"
@@ -1397,11 +1398,9 @@ static void parse_args(Toxic *toxic, int argc, char *argv[])
                 }
 
                 snprintf(run_opts->config_path, sizeof(run_opts->config_path), "%s", optarg);
+                run_opts->use_custom_config_file = true;
 
-                if (!file_exists(run_opts->config_path)) {
-                    queue_init_message("Config file not found");
-                }
-
+                queue_init_message("Using '%s' custom config file", run_opts->config_path);
                 break;
             }
 
@@ -1453,7 +1452,7 @@ static void parse_args(Toxic *toxic, int argc, char *argv[])
                 strcpy(client_data->block_path, optarg);
                 strcat(client_data->block_path, "-blocklist");
 
-                queue_init_message("Using '%s' data file", client_data->data_path);
+                queue_init_message("Using '%s' tox profile", client_data->data_path);
 
                 break;
             }
@@ -1708,14 +1707,20 @@ int main(int argc, char **argv)
         first_time_encrypt(&toxic->client_data, "Encrypt existing data file? Y/n (q to quit)");
     }
 
-    const char *config_path = !string_is_empty(run_opts->config_path) ? run_opts->config_path : NULL;
+    if (!settings_load_config_file(run_opts, toxic->client_data.data_path)) {
+        queue_init_message("Failed to load config file");
+    }
 
-    const int ms_ret = settings_load_main(toxic->c_config, config_path);
+    const int ms_ret = settings_load_main(toxic->c_config, run_opts);
 
     if (ms_ret < 0) {
         queue_init_message("Failed to load user settings: error %d", ms_ret);
     }
 
+    if (!run_opts->use_custom_config_file && run_opts->use_custom_data) {
+        queue_init_message("Using '%s' config file", run_opts->config_path);
+    }
+
     const int curl_init = curl_global_init(CURL_GLOBAL_ALL);
     const int nameserver_ret = name_lookup_init(run_opts->nameserver_path, curl_init);
 
@@ -1753,19 +1758,19 @@ int main(int argc, char **argv)
     load_groups(toxic);
     load_conferences(toxic);
 
-    const int fs_ret = settings_load_friends(config_path);
+    const int fs_ret = settings_load_friends(run_opts);
 
     if (fs_ret != 0) {
         queue_init_message("Failed to load friend config settings: error %d", fs_ret);
     }
 
-    const int gs_ret = settings_load_groups(config_path);
+    const int gs_ret = settings_load_groups(run_opts);
 
     if (gs_ret != 0) {
         queue_init_message("Failed to load groupchat config settings: error %d", gs_ret);
     }
 
-    const int cs_ret = settings_load_conferences(config_path);
+    const int cs_ret = settings_load_conferences(run_opts);
 
     if (cs_ret != 0) {
         queue_init_message("Failed to load conference config settings: error %d", cs_ret);
diff --git a/src/toxic.h b/src/toxic.h
index 9c9ad0ebd..102b49ecd 100644
--- a/src/toxic.h
+++ b/src/toxic.h
@@ -51,31 +51,6 @@
 #include "settings.h"
 #include "toxic_constants.h"
 
-typedef struct Run_Options {
-    bool use_ipv4;
-    bool force_tcp;
-    bool disable_local_discovery;
-    bool debug;
-    bool default_locale;
-    bool use_custom_data;
-    bool no_connect;
-    bool encrypt_data;
-    bool unencrypt_data;
-
-    char nameserver_path[MAX_STR_SIZE];
-    char config_path[MAX_STR_SIZE];
-    char nodes_path[MAX_STR_SIZE];
-
-    bool logging;
-    FILE *log_fp;
-
-    char proxy_address[256];
-    uint8_t proxy_type;
-    uint16_t proxy_port;
-
-    uint16_t tcp_port;
-} Run_Options;
-
 typedef struct Client_Data {
     bool is_encrypted;
     char pass[MAX_PASSWORD_LEN + 1];
@@ -86,6 +61,7 @@ typedef struct Client_Data {
 
 typedef struct ToxAV ToxAV;
 typedef struct ToxWindow ToxWindow;
+typedef struct Run_Options Run_Options;
 
 typedef struct Toxic {
     Tox   *tox;