diff --git a/src/oauth.rs b/src/oauth.rs
index 5627900..f5659da 100644
--- a/src/oauth.rs
+++ b/src/oauth.rs
@@ -15,6 +15,8 @@ const REDDIT_ANDROID_OAUTH_CLIENT_ID: &str = "ohXpoqrZYub1kg";
 
 const AUTH_ENDPOINT: &str = "https://www.reddit.com";
 
+const OAUTH_TIMEOUT: Duration = Duration::from_secs(5);
+
 // Spoofed client for Android devices
 #[derive(Debug, Clone, Default)]
 pub struct Oauth {
@@ -32,24 +34,30 @@ impl Oauth {
 		loop {
 			let attempt = Self::new_with_timeout().await;
 			match attempt {
-				Ok(Some(oauth)) => {
+				Ok(Ok(oauth)) => {
 					info!("[✅] Successfully created OAuth client");
 					return oauth;
 				}
-				Ok(None) => {
-					error!("Failed to create OAuth client. Retrying in 5 seconds...");
+				Ok(Err(e)) => {
+					error!("Failed to create OAuth client: {}. Retrying in 5 seconds...", {
+						match e {
+							AuthError::Hyper(error) => error.to_string(),
+							AuthError::SerdeDeserialize(error) => error.to_string(),
+							AuthError::Field((value, error)) => format!("{error}\n{value}"),
+						}
+					});
 				}
-				Err(duration) => {
-					error!("Failed to create OAuth client in {duration:?}. Retrying in 5 seconds...");
+				Err(_) => {
+					error!("Failed to create OAuth client before timeout. Retrying in 5 seconds...");
 				}
 			}
-			tokio::time::sleep(Duration::from_secs(5)).await;
+			tokio::time::sleep(OAUTH_TIMEOUT).await;
 		}
 	}
 
-	async fn new_with_timeout() -> Result<Option<Self>, Elapsed> {
+	async fn new_with_timeout() -> Result<Result<Self, AuthError>, Elapsed> {
 		let mut oauth = Self::default();
-		timeout(Duration::from_secs(5), oauth.login()).await.map(|result| result.map(|_| oauth))
+		timeout(OAUTH_TIMEOUT, oauth.login()).await.map(|result: Result<(), AuthError>| result.map(|_| oauth))
 	}
 
 	pub(crate) fn default() -> Self {
@@ -66,7 +74,7 @@ impl Oauth {
 			device,
 		}
 	}
-	async fn login(&mut self) -> Option<()> {
+	async fn login(&mut self) -> Result<(), AuthError> {
 		// Construct URL for OAuth token
 		let url = format!("{AUTH_ENDPOINT}/auth/v2/oauth/access-token/loid");
 		let mut builder = Request::builder().method(Method::POST).uri(&url);
@@ -95,7 +103,7 @@ impl Oauth {
 
 		// Send request
 		let client: &once_cell::sync::Lazy<client::Client<_, Body>> = &CLIENT;
-		let resp = client.request(request).await.ok()?;
+		let resp = client.request(request).await?;
 
 		trace!("Received response with status {} and length {:?}", resp.status(), resp.headers().get("content-length"));
 		trace!("OAuth headers: {:#?}", resp.headers());
@@ -106,30 +114,58 @@ impl Oauth {
 		// Not worried about the privacy implications, since this is randomly changed
 		// and really only as privacy-concerning as the OAuth token itself.
 		if let Some(header) = resp.headers().get("x-reddit-loid") {
-			self.headers_map.insert("x-reddit-loid".to_owned(), header.to_str().ok()?.to_string());
+			self.headers_map.insert("x-reddit-loid".to_owned(), header.to_str().unwrap().to_string());
 		}
 
 		// Same with x-reddit-session
 		if let Some(header) = resp.headers().get("x-reddit-session") {
-			self.headers_map.insert("x-reddit-session".to_owned(), header.to_str().ok()?.to_string());
+			self.headers_map.insert("x-reddit-session".to_owned(), header.to_str().unwrap().to_string());
 		}
 
 		trace!("Serializing response...");
 
 		// Serialize response
-		let body_bytes = hyper::body::to_bytes(resp.into_body()).await.ok()?;
-		let json: serde_json::Value = serde_json::from_slice(&body_bytes).ok()?;
+		let body_bytes = hyper::body::to_bytes(resp.into_body()).await?;
+		let json: serde_json::Value = serde_json::from_slice(&body_bytes)?;
 
 		trace!("Accessing relevant fields...");
 
 		// Save token and expiry
-		self.token = json.get("access_token")?.as_str()?.to_string();
-		self.expires_in = json.get("expires_in")?.as_u64()?;
+		self.token = json
+			.get("access_token")
+			.ok_or_else(|| AuthError::Field((json.clone(), "access_token")))?
+			.as_str()
+			.ok_or_else(|| AuthError::Field((json.clone(), "access_token: as_str")))?
+			.to_string();
+		self.expires_in = json
+			.get("expires_in")
+			.ok_or_else(|| AuthError::Field((json.clone(), "expires_in")))?
+			.as_u64()
+			.ok_or_else(|| AuthError::Field((json.clone(), "expires_in: as_u64")))?;
 		self.headers_map.insert("Authorization".to_owned(), format!("Bearer {}", self.token));
 
 		info!("[✅] Success - Retrieved token \"{}...\", expires in {}", &self.token[..32], self.expires_in);
 
-		Some(())
+		Ok(())
+	}
+}
+
+#[derive(Debug)]
+enum AuthError {
+	Hyper(hyper::Error),
+	SerdeDeserialize(serde_json::Error),
+	Field((serde_json::Value, &'static str)),
+}
+
+impl From<hyper::Error> for AuthError {
+	fn from(err: hyper::Error) -> Self {
+		AuthError::Hyper(err)
+	}
+}
+
+impl From<serde_json::Error> for AuthError {
+	fn from(err: serde_json::Error) -> Self {
+		AuthError::SerdeDeserialize(err)
 	}
 }