diff --git a/conduwuit-example.toml b/conduwuit-example.toml
index a980efaf3..9a478fa0c 100644
--- a/conduwuit-example.toml
+++ b/conduwuit-example.toml
@@ -2174,7 +2174,11 @@
 #connection_uri =
 
 # Same as `connection_uri`, except loaded from a file. If `connection_uri`
-# is defined, it is prioritized and `connection_uri_file` is ignored
+# is defined, it is prioritized and `connection_uri_file` is ignored.
+#
+# The file will be read once, when Continuwuity starts. It is not
+# currently reread when the server configuration is reloaded. If the file
+# cannot be read, Continuwuity will fail to start.
 #
 #connection_uri_file =
 
diff --git a/src/core/config/check.rs b/src/core/config/check.rs
index 4b053403a..866d330cf 100644
--- a/src/core/config/check.rs
+++ b/src/core/config/check.rs
@@ -1,4 +1,4 @@
-use std::{env::consts::OS, path::PathBuf};
+use std::env::consts::OS;
 
 use either::Either;
 use figment::Figment;
@@ -264,14 +264,14 @@ pub fn check(config: &Config) -> Result {
 	}
 
 	if config.smtp.as_ref().is_some_and(|f| {
-		f.connection_uri.is_none() && f.connection_uri_file.is_none()
-			|| (f.connection_uri == Some(String::new())
-				&& f.connection_uri_file == Some(PathBuf::new()))
+		f.connection_uri.as_ref().is_none_or(String::is_empty)
+			&& f.connection_uri_file
+				.as_ref()
+				.is_none_or(|f| f.as_os_str().is_empty())
 	}) {
 		return Err!(Config(
 			"connection_uri",
-			"If smtp is enabled, either connection_uri or connection_uri_file has to be \
-			 defined."
+			"If smtp is enabled, either connection_uri or connection_uri_file has to be defined."
 		));
 	}
 
diff --git a/src/core/config/mod.rs b/src/core/config/mod.rs
index ea6aeb5e8..13358d59b 100644
--- a/src/core/config/mod.rs
+++ b/src/core/config/mod.rs
@@ -2592,7 +2592,11 @@ pub struct SmtpConfig {
 	pub connection_uri: Option<String>,
 
 	/// Same as `connection_uri`, except loaded from a file. If `connection_uri`
-	/// is defined, it is prioritized and `connection_uri_file` is ignored
+	/// is defined, it is prioritized and `connection_uri_file` is ignored.
+	///
+	/// The file will be read once, when Continuwuity starts. It is not
+	/// currently reread when the server configuration is reloaded. If the file
+	/// cannot be read, Continuwuity will fail to start.
 	pub connection_uri_file: Option<PathBuf>,
 
 	/// The outgoing address which will be used for sending emails.
diff --git a/src/service/mailer/mod.rs b/src/service/mailer/mod.rs
index 9126769c1..cefecfdcb 100644
--- a/src/service/mailer/mod.rs
+++ b/src/service/mailer/mod.rs
@@ -20,28 +20,27 @@ pub struct Service {
 #[async_trait::async_trait]
 impl crate::Service for Service {
 	fn build(args: Args<'_>) -> Result<Arc<Self>> {
-		let transport =
-			args.server
-				.config
-				.smtp
-				.as_ref()
-				.map(|config| -> Result<_> {
-					let connection_uri: String =
-						if let Some(uri) = &config.connection_uri {
-							uri.clone()
-						} else {
-							std::fs::read_to_string(
-								config.connection_uri_file.as_ref().unwrap() // Safe to unwrap here assuming the config checks properly run and throw errors
-							)
-							.map_err(|err| err!("Failed to read SMTP connection URI file: {err}"))?
-						};
-					let transport = Transport::from_url(&connection_uri)
-						.map_err(|err| err!("Failed to set up SMTP transport: {err}"))?
-						.build();
+		let transport = args
+			.server
+			.config
+			.smtp
+			.as_ref()
+			.map(|config| -> Result<_> {
+				let connection_uri = match (&config.connection_uri, &config.connection_uri_file) {
+					| (Some(uri), _) => uri.clone(),
+					| (None, Some(path)) => std::fs::read_to_string(path)
+						.map_err(|err| err!("Failed to read SMTP connection URI file: {err}"))?,
+					| (None, None) => unreachable!(
+						"Config validation should guarantee one SMTP connection source."
+					),
+				};
+				let transport = Transport::from_url(&connection_uri)
+					.map_err(|err| err!("Failed to set up SMTP transport: {err}"))?
+					.build();
 
-					Ok((config.sender.clone(), transport))
-				})
-				.transpose()?;
+				Ok((config.sender.clone(), transport))
+			})
+			.transpose()?;
 
 		Ok(Arc::new(Self { transport }))
 	}