diff --git a/espanso/src/cli/launcher/mod.rs b/espanso/src/cli/launcher/mod.rs
index ad354ca..b7989ff 100644
--- a/espanso/src/cli/launcher/mod.rs
+++ b/espanso/src/cli/launcher/mod.rs
@@ -17,8 +17,10 @@
  * along with espanso.  If not, see <https://www.gnu.org/licenses/>.
  */
 
+use log::{error};
 use self::util::MigrationError;
 use crate::preferences::Preferences;
+use crate::exit_code::{LAUNCHER_CONFIG_DIR_POPULATION_FAILURE, LAUNCHER_SUCCESS};
 
 use super::{CliModule, CliModuleArgs};
 
@@ -161,7 +163,14 @@ fn launcher_main(args: CliModuleArgs) -> i32 {
     true
   };
 
-  // TODO: initialize config directory if not present
+  if !espanso_config::is_legacy_config(&paths.config) {
+    if let Err(err) = crate::config::populate_default_config(&paths.config) {
+      error!("Error populating the config directory: {:?}", err);
+
+      // TODO: show an error message with GUI
+      return LAUNCHER_CONFIG_DIR_POPULATION_FAILURE;
+    }
+  }
 
   if should_launch_daemon {
     // We hide the dock icon on macOS to avoid having it around when the daemon is running
@@ -173,7 +182,7 @@ fn launcher_main(args: CliModuleArgs) -> i32 {
     daemon::launch_daemon(&paths_overrides).expect("failed to launch daemon");
   }
 
-  0
+  LAUNCHER_SUCCESS
 }
 
 #[cfg(not(feature = "modulo"))]
diff --git a/espanso/src/config.rs b/espanso/src/config.rs
new file mode 100644
index 0000000..4c36588
--- /dev/null
+++ b/espanso/src/config.rs
@@ -0,0 +1,58 @@
+/*
+ * This file is part of espanso.
+ *
+ * Copyright (C) 2019-2021 Federico Terzi
+ *
+ * espanso 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.
+ *
+ * espanso 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 espanso.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+use anyhow::Result;
+use log::info;
+use std::path::Path;
+
+const DEFAULT_CONFIG_FILE_CONTENT: &str = include_str!("./res/config/default.yml");
+const DEFAULT_MATCH_FILE_CONTENT: &str = include_str!("./res/config/base.yml"); 
+
+pub fn populate_default_config(config_dir: &Path) -> Result<()> {
+  if !config_dir.is_dir() {
+    info!("generating base configuration directory in: {:?}", config_dir);
+    std::fs::create_dir_all(config_dir)?;
+  }
+
+  let sub_config_dir = config_dir.join("config");
+  let sub_match_dir = config_dir.join("match");
+
+  if !sub_config_dir.is_dir() {
+    info!("generating config directory in: {:?}", sub_config_dir);
+    std::fs::create_dir_all(&sub_config_dir)?;
+  }
+  if !sub_match_dir.is_dir() {
+    info!("generating match directory in: {:?}", sub_match_dir);
+    std::fs::create_dir_all(&sub_match_dir)?;
+  }
+
+  let default_file = sub_config_dir.join("default.yml");
+  let match_file = sub_match_dir.join("base.yml");
+
+  if !default_file.is_file() {
+    info!("populating default.yml file with initial content: {:?}", default_file);
+    std::fs::write(default_file, DEFAULT_CONFIG_FILE_CONTENT)?;
+  }
+  if !match_file.is_file() {
+    info!("populating base.yml file with initial content: {:?}", match_file);
+    std::fs::write(match_file, DEFAULT_MATCH_FILE_CONTENT)?;
+  }
+
+  Ok(())
+}
\ No newline at end of file
diff --git a/espanso/src/exit_code.rs b/espanso/src/exit_code.rs
index d97b81e..58ccae7 100644
--- a/espanso/src/exit_code.rs
+++ b/espanso/src/exit_code.rs
@@ -40,6 +40,9 @@ pub const MIGRATE_UNEXPECTED_FAILURE: i32 = 101;
 pub const ADD_TO_PATH_SUCCESS: i32 = 0;
 pub const ADD_TO_PATH_FAILURE: i32 = 1;
 
+pub const LAUNCHER_SUCCESS: i32 = 0;
+pub const LAUNCHER_CONFIG_DIR_POPULATION_FAILURE: i32 = 1;
+
 use std::sync::Mutex;
 
 lazy_static! {
diff --git a/espanso/src/main.rs b/espanso/src/main.rs
index 28fe541..e708277 100644
--- a/espanso/src/main.rs
+++ b/espanso/src/main.rs
@@ -36,6 +36,7 @@ use simplelog::{
 use crate::cli::{LogMode, PathsOverrides};
 
 mod cli;
+mod config;
 mod engine;
 mod exit_code;
 mod gui;
diff --git a/espanso/src/res/config/base.yml b/espanso/src/res/config/base.yml
new file mode 100644
index 0000000..c082c9a
--- /dev/null
+++ b/espanso/src/res/config/base.yml
@@ -0,0 +1,37 @@
+# espanso match file
+
+# For a complete introduction, visit the official docs at: https://espanso.org/docs/
+
+# You can use this file to define the base matches (aka snippets)
+# that will be available in every application when using espanso.
+
+# Matches are substitution rules: when you type the "trigger" string
+# it gets replaced by the "replace" string.
+matches:
+  # Simple text replacement
+  - trigger: ":espanso"
+    replace: "Hi there!"
+
+  # NOTE: espanso uses YAML to define matches, so pay attention to the indentation!
+
+  # But matches can also be dynamic:
+
+  # Print the current date
+  - trigger: ":date"
+    replace: "{{mydate}}"
+    vars:
+      - name: mydate
+        type: date
+        params:
+          format: "%m/%d/%Y"
+
+  # Print the output of a shell command
+  - trigger: ":shell"
+    replace: "{{output}}"
+    vars:
+      - name: output
+        type: shell
+        params:
+          cmd: "echo Hello from your shell"
+
+  # And much more! For more information, visit the docs: https://espanso.org/docs/
\ No newline at end of file
diff --git a/espanso/src/res/config/default.yml b/espanso/src/res/config/default.yml
new file mode 100644
index 0000000..4f52b02
--- /dev/null
+++ b/espanso/src/res/config/default.yml
@@ -0,0 +1,40 @@
+# espanso configuration file
+
+# For a complete introduction, visit the official docs at: https://espanso.org/docs/
+
+# You can use this file to define the global configuration options for espanso.
+# These are the parameters that will be used by default on every application,
+# but you can also override them on a per-application basis.
+
+# To make customization easier, this file contains some of the commonly used
+# parameters. Feel free to uncomment and tune them to fit your needs!
+
+# --- Toggle key
+
+# Customize the key used to disable and enable espanso (when double tapped)
+# Available options: CTRL, SHIFT, ALT, CMD, OFF
+# You can also specify the key variant, such as LEFT_CTRL, RIGHT_SHIFT, etc...
+# toggle_key: ALT
+# You can also disable the toggle key completely with
+# toggle_key: OFF
+
+# --- Injection Backend
+
+# Espanso supports multiple ways of injecting text into applications. Each of
+# them has its quirks, therefore you may want to change it if you are having problems.
+# By default, espanso uses the "Auto" backend which should work well in most cases,
+# but you may want to try the "Clipboard" or "Inject" backend in case of issues.
+# backend: Clipboard
+
+# --- Auto-restart
+
+# Enable/disable the config auto-reload after a file change is detected.
+# auto_restart: false
+
+# --- Clipboard threshold
+
+# Because injecting long texts char-by-char is a slow operation, espanso automatically
+# uses the clipboard if the text is longer than 'clipboard_threshold' characters.
+# clipboard_threshold: 100
+
+# For a list of all the available options, visit the official docs at: https://espanso.org/docs/
\ No newline at end of file