diff --git a/rama-http-backend/src/client/proxy/layer/mod.rs b/rama-http-backend/src/client/proxy/layer/mod.rs
index a2949490..26f08afe 100644
--- a/rama-http-backend/src/client/proxy/layer/mod.rs
+++ b/rama-http-backend/src/client/proxy/layer/mod.rs
@@ -8,4 +8,4 @@ pub use proxy_auth_header::{SetProxyAuthHttpHeaderLayer, SetProxyAuthHttpHeaderS
 
 mod proxy_connector;
 #[doc(inline)]
-pub use proxy_connector::{HttpProxyConnector, HttpProxyConnectorLayer};
+pub use proxy_connector::{HttpProxyConnector, HttpProxyConnectorLayer, HttpProxyError};
diff --git a/rama-http-backend/src/client/proxy/layer/proxy_connector/connector.rs b/rama-http-backend/src/client/proxy/layer/proxy_connector/connector.rs
index 734077c8..436d24df 100644
--- a/rama-http-backend/src/client/proxy/layer/proxy_connector/connector.rs
+++ b/rama-http-backend/src/client/proxy/layer/proxy_connector/connector.rs
@@ -11,6 +11,8 @@ use rama_http_types::{
 use rama_net::{address::Authority, stream::Stream};
 use tokio::io::{AsyncReadExt, AsyncWriteExt};
 
+use super::HttpProxyError;
+
 #[derive(Debug, Clone)]
 /// Connector for HTTP proxies.
 ///
@@ -64,7 +66,7 @@ impl InnerHttpProxyConnector {
     pub(super) async fn handshake<S: Stream + Unpin>(
         &self,
         mut stream: S,
-    ) -> Result<S, std::io::Error> {
+    ) -> Result<S, HttpProxyError> {
         // TODO: handle user-agent and host better
         // TODO: use h1 protocol from embedded hyper directly here!
         let mut request = format!(
@@ -100,7 +102,8 @@ impl InnerHttpProxyConnector {
                 return Err(std::io::Error::new(
                     std::io::ErrorKind::UnexpectedEof,
                     "http conn handshake read incomplete",
-                ));
+                )
+                .into());
             }
             pos += n;
 
@@ -113,27 +116,24 @@ impl InnerHttpProxyConnector {
                     return Err(std::io::Error::new(
                         std::io::ErrorKind::InvalidData,
                         "http conn handshake response too large",
-                    ));
+                    )
+                    .into());
                 }
             // else read more
             } else if recvd.starts_with(b"HTTP/1.1 407") {
-                return Err(std::io::Error::new(
-                    std::io::ErrorKind::PermissionDenied,
-                    "http conn handshake proxy auth required",
-                ));
+                return Err(HttpProxyError::AuthRequired);
+            } else if recvd.starts_with(b"HTTP/1.1 503") {
+                return Err(HttpProxyError::Unavailable);
             } else {
                 let input = String::from_utf8_lossy(recvd);
-                return Err(std::io::Error::new(
-                    std::io::ErrorKind::InvalidData,
-                    format!(
-                        "invalid http conn handshake start: [{}]",
-                        if let Some((line, _)) = input.split_once("\r\n") {
-                            Cow::Borrowed(line)
-                        } else {
-                            input
-                        }
-                    ),
-                ));
+                return Err(HttpProxyError::Other(format!(
+                    "invalid http conn handshake start: [{}]",
+                    if let Some((line, _)) = input.split_once("\r\n") {
+                        Cow::Borrowed(line)
+                    } else {
+                        input
+                    }
+                )));
             }
         }
     }
diff --git a/rama-http-backend/src/client/proxy/layer/proxy_connector/mod.rs b/rama-http-backend/src/client/proxy/layer/proxy_connector/mod.rs
index 5b62c360..c4d3fa4a 100644
--- a/rama-http-backend/src/client/proxy/layer/proxy_connector/mod.rs
+++ b/rama-http-backend/src/client/proxy/layer/proxy_connector/mod.rs
@@ -2,6 +2,10 @@ mod connector;
 // internal usage only
 use connector::InnerHttpProxyConnector;
 
+mod proxy_error;
+#[doc(inline)]
+pub use proxy_error::HttpProxyError;
+
 mod layer;
 #[doc(inline)]
 pub use layer::HttpProxyConnectorLayer;
diff --git a/rama-http-backend/src/client/proxy/layer/proxy_connector/proxy_error.rs b/rama-http-backend/src/client/proxy/layer/proxy_connector/proxy_error.rs
new file mode 100644
index 00000000..ada4a776
--- /dev/null
+++ b/rama-http-backend/src/client/proxy/layer/proxy_connector/proxy_error.rs
@@ -0,0 +1,59 @@
+use std::fmt;
+
+#[derive(Debug)]
+/// error that can be returned in case a http proxy
+/// did not manage to establish a connection
+pub enum HttpProxyError {
+    /// Proxy Authentication Required
+    ///
+    /// (Proxy returned HTTP 407)
+    AuthRequired,
+    /// Proxy is Unavailable
+    ///
+    /// (Proxy returned HTTP 503)
+    Unavailable,
+    /// I/O error happened as part of HTTP Proxy Connection Establishment
+    ///
+    /// (e.g. some kind of TCP error)
+    Transport(std::io::Error),
+    /// Something went wrong, but classification did not happen.
+    ///
+    /// (First header line of http response is included in error)
+    Other(String),
+}
+
+impl fmt::Display for HttpProxyError {
+    fn fmt(&self, f: &mut fmt::Formatter<'_>) -> fmt::Result {
+        match self {
+            HttpProxyError::AuthRequired => {
+                write!(f, "http proxy error: proxy auth required (http 407)")
+            }
+            HttpProxyError::Unavailable => {
+                write!(f, "http proxy error: proxy unavailable (http 503)")
+            }
+            HttpProxyError::Transport(error) => {
+                write!(f, "http proxy error: transport error: I/O [{}]", error)
+            }
+            HttpProxyError::Other(header) => {
+                write!(f, "http proxy error: first line of header = [{}]", header)
+            }
+        }
+    }
+}
+
+impl From<std::io::Error> for HttpProxyError {
+    fn from(value: std::io::Error) -> Self {
+        Self::Transport(value)
+    }
+}
+
+impl std::error::Error for HttpProxyError {
+    fn source(&self) -> Option<&(dyn std::error::Error + 'static)> {
+        match self {
+            HttpProxyError::AuthRequired => None,
+            HttpProxyError::Unavailable => None,
+            HttpProxyError::Transport(err) => Some(err),
+            HttpProxyError::Other(_) => None,
+        }
+    }
+}