diff --git a/src/app.rs b/src/app.rs
index 3a1da3e..93b9da4 100644
--- a/src/app.rs
+++ b/src/app.rs
@@ -1,7 +1,7 @@
 use std::fs;
 use std::path::PathBuf;
 
-use crate::db::DB;
+use crate::db::{self, DB};
 use crate::paths::Paths;
 
 pub mod config;
@@ -17,6 +17,18 @@ pub mod vfs;
 #[cfg(test)]
 pub mod test;
 
+#[derive(thiserror::Error, Debug)]
+pub enum Error {
+	#[error(transparent)]
+	Config(#[from] config::Error),
+	#[error(transparent)]
+	Database(#[from] db::Error),
+	#[error("Filesystem error for `{0}`: `{1}`")]
+	Io(PathBuf, std::io::Error),
+	#[error(transparent)]
+	Settings(#[from] settings::Error),
+}
+
 #[derive(Clone)]
 pub struct App {
 	pub port: u16,
@@ -36,12 +48,16 @@ pub struct App {
 }
 
 impl App {
-	pub fn new(port: u16, paths: Paths) -> anyhow::Result<Self> {
+	pub fn new(port: u16, paths: Paths) -> Result<Self, Error> {
 		let db = DB::new(&paths.db_file_path)?;
-		fs::create_dir_all(&paths.web_dir_path)?;
-		fs::create_dir_all(&paths.swagger_dir_path)?;
+		fs::create_dir_all(&paths.web_dir_path)
+			.map_err(|e| Error::Io(paths.web_dir_path.clone(), e))?;
+		fs::create_dir_all(&paths.swagger_dir_path)
+			.map_err(|e| Error::Io(paths.swagger_dir_path.clone(), e))?;
 
 		let thumbnails_dir_path = paths.cache_dir_path.join("thumbnails");
+		fs::create_dir_all(&thumbnails_dir_path)
+			.map_err(|e| Error::Io(thumbnails_dir_path.clone(), e))?;
 
 		let vfs_manager = vfs::Manager::new(db.clone());
 		let settings_manager = settings::Manager::new(db.clone());
diff --git a/src/app/config.rs b/src/app/config.rs
index f50a52d..c20c608 100644
--- a/src/app/config.rs
+++ b/src/app/config.rs
@@ -1,6 +1,6 @@
 use serde::Deserialize;
 use std::io::Read;
-use std::path;
+use std::path::{Path, PathBuf};
 
 use crate::app::{ddns, settings, user, vfs};
 
@@ -8,9 +8,13 @@ use crate::app::{ddns, settings, user, vfs};
 pub enum Error {
 	#[error(transparent)]
 	Ddns(#[from] ddns::Error),
+	#[error("Filesystem error for `{0}`: `{1}`")]
+	Io(PathBuf, std::io::Error),
 	#[error(transparent)]
 	Settings(#[from] settings::Error),
 	#[error(transparent)]
+	Toml(#[from] toml::de::Error),
+	#[error(transparent)]
 	User(#[from] user::Error),
 	#[error(transparent)]
 	Vfs(#[from] vfs::Error),
@@ -25,10 +29,13 @@ pub struct Config {
 }
 
 impl Config {
-	pub fn from_path(path: &path::Path) -> anyhow::Result<Config> {
-		let mut config_file = std::fs::File::open(path)?;
+	pub fn from_path(path: &Path) -> Result<Config, Error> {
+		let mut config_file =
+			std::fs::File::open(path).map_err(|e| Error::Io(path.to_owned(), e))?;
 		let mut config_file_content = String::new();
-		config_file.read_to_string(&mut config_file_content)?;
+		config_file
+			.read_to_string(&mut config_file_content)
+			.map_err(|e| Error::Io(path.to_owned(), e))?;
 		let config = toml::de::from_str::<Self>(&config_file_content)?;
 		Ok(config)
 	}
diff --git a/src/service/error.rs b/src/service/error.rs
index e5a62c5..ad4c406 100644
--- a/src/service/error.rs
+++ b/src/service/error.rs
@@ -48,7 +48,9 @@ impl From<config::Error> for APIError {
 	fn from(error: config::Error) -> APIError {
 		match error {
 			config::Error::Ddns(e) => e.into(),
+			config::Error::Io(_, _) => APIError::Internal,
 			config::Error::Settings(e) => e.into(),
+			config::Error::Toml(_) => APIError::Internal,
 			config::Error::User(e) => e.into(),
 			config::Error::Vfs(e) => e.into(),
 		}