diff --git a/src/admin/server/commands.rs b/src/admin/server/commands.rs
index 6027a9eb..8c3573f0 100644
--- a/src/admin/server/commands.rs
+++ b/src/admin/server/commands.rs
@@ -30,10 +30,31 @@ pub(super) async fn show_config(&self) -> Result {
 
 #[admin_command]
 pub(super) async fn reload_config(&self, path: Option<PathBuf>) -> Result {
-	let path = path.as_deref().into_iter();
-	self.services.config.reload(path)?;
+	// The path argument is only what's optionally passed via the admin command,
+	// so we need to merge it with the existing paths if any were given at startup.
+	let mut paths = Vec::new();
 
-	self.write_str("Successfully reconfigured.").await
+	// Add previously saved paths to the argument list
+	self.services
+		.config
+		.config_paths
+		.clone()
+		.unwrap_or_default()
+		.iter()
+		.for_each(|p| paths.push(p.to_owned()));
+
+	// If a path is given, and it's not already in the list,
+	// add it last, so that it overrides earlier files
+	if let Some(p) = path {
+		if !paths.contains(&p) {
+			paths.push(p);
+		}
+	}
+
+	self.services.config.reload(&paths)?;
+
+	self.write_str(&format!("Successfully reconfigured from paths: {paths:?}"))
+		.await
 }
 
 #[admin_command]
diff --git a/src/core/config/mod.rs b/src/core/config/mod.rs
index c60d3115..5dcaff5c 100644
--- a/src/core/config/mod.rs
+++ b/src/core/config/mod.rs
@@ -6,7 +6,7 @@ pub mod proxy;
 use std::{
 	collections::{BTreeMap, BTreeSet},
 	net::{IpAddr, Ipv4Addr, Ipv6Addr, SocketAddr},
-	path::{Path, PathBuf},
+	path::PathBuf,
 };
 
 use conduwuit_macros::config_example_generator;
@@ -53,9 +53,13 @@ use crate::{Result, err, error::Error, utils::sys};
 ### For more information, see:
 ### https://continuwuity.org/configuration.html
 "#,
-	ignore = "catchall well_known tls blurhashing allow_invalid_tls_certificates_yes_i_know_what_the_fuck_i_am_doing_with_this_and_i_know_this_is_insecure"
+	ignore = "config_paths catchall well_known tls blurhashing allow_invalid_tls_certificates_yes_i_know_what_the_fuck_i_am_doing_with_this_and_i_know_this_is_insecure"
 )]
 pub struct Config {
+	// Paths to config file(s). Not supposed to be set manually in the config file,
+	// only updated dynamically from the --config option given at runtime.
+	pub config_paths: Option<Vec<PathBuf>>,
+
 	/// The server_name is the pretty name of this server. It is used as a
 	/// suffix for user and room IDs/aliases.
 	///
@@ -2226,26 +2230,24 @@ const DEPRECATED_KEYS: &[&str; 9] = &[
 
 impl Config {
 	/// Pre-initialize config
-	pub fn load<'a, I>(paths: I) -> Result<Figment>
-	where
-		I: Iterator<Item = &'a Path>,
-	{
+	pub fn load(paths: &[PathBuf]) -> Result<Figment> {
 		let envs = [
 			Env::var("CONDUIT_CONFIG"),
 			Env::var("CONDUWUIT_CONFIG"),
 			Env::var("CONTINUWUITY_CONFIG"),
 		];
-
-		let config = envs
+		let mut config = envs
 			.into_iter()
 			.flatten()
 			.map(Toml::file)
-			.chain(paths.map(Toml::file))
+			.chain(paths.iter().cloned().map(Toml::file))
 			.fold(Figment::new(), |config, file| config.merge(file.nested()))
 			.merge(Env::prefixed("CONDUIT_").global().split("__"))
 			.merge(Env::prefixed("CONDUWUIT_").global().split("__"))
 			.merge(Env::prefixed("CONTINUWUITY_").global().split("__"));
 
+		config = config.join(("config_paths", paths));
+
 		Ok(config)
 	}
 
diff --git a/src/main/server.rs b/src/main/server.rs
index b060dc5a..4c1abc25 100644
--- a/src/main/server.rs
+++ b/src/main/server.rs
@@ -1,4 +1,4 @@
-use std::{path::PathBuf, sync::Arc};
+use std::sync::Arc;
 
 use conduwuit_core::{
 	Error, Result,
@@ -38,14 +38,9 @@ impl Server {
 	) -> Result<Arc<Self>, Error> {
 		let _runtime_guard = runtime.map(runtime::Handle::enter);
 
-		let config_paths = args
-			.config
-			.as_deref()
-			.into_iter()
-			.flat_map(<[_]>::iter)
-			.map(PathBuf::as_path);
+		let config_paths = args.config.clone().unwrap_or_default();
 
-		let config = Config::load(config_paths)
+		let config = Config::load(&config_paths)
 			.and_then(|raw| update(raw, args))
 			.and_then(|raw| Config::new(&raw))?;
 
diff --git a/src/service/config/mod.rs b/src/service/config/mod.rs
index 414c22b6..efeed743 100644
--- a/src/service/config/mod.rs
+++ b/src/service/config/mod.rs
@@ -1,4 +1,4 @@
-use std::{iter, ops::Deref, path::Path, sync::Arc};
+use std::{ops::Deref, path::PathBuf, sync::Arc};
 
 use async_trait::async_trait;
 use conduwuit::{
@@ -51,7 +51,8 @@ fn handle_reload(&self) -> Result {
 		])
 		.expect("failed to notify systemd of reloading state");
 
-		self.reload(iter::empty())?;
+		let config_paths = self.server.config.config_paths.clone().unwrap_or_default();
+		self.reload(&config_paths)?;
 
 		#[cfg(all(feature = "systemd", target_os = "linux"))]
 		sd_notify::notify(false, &[sd_notify::NotifyState::Ready])
@@ -62,10 +63,7 @@ fn handle_reload(&self) -> Result {
 }
 
 #[implement(Service)]
-pub fn reload<'a, I>(&self, paths: I) -> Result<Arc<Config>>
-where
-	I: Iterator<Item = &'a Path>,
-{
+pub fn reload(&self, paths: &[PathBuf]) -> Result<Arc<Config>> {
 	let old = self.server.config.clone();
 	let new = Config::load(paths).and_then(|raw| Config::new(&raw))?;