diff --git a/aquatic_http/src/lib/network/connection.rs b/aquatic_http/src/lib/network/connection.rs
index aa6e6a0..60c9811 100644
--- a/aquatic_http/src/lib/network/connection.rs
+++ b/aquatic_http/src/lib/network/connection.rs
@@ -4,7 +4,7 @@ use std::io::{Read, Write};
 use std::sync::Arc;
 
 use hashbrown::HashMap;
-use mio::Token;
+use mio::{Token, Poll};
 use mio::net::TcpStream;
 use native_tls::{TlsAcceptor, MidHandshakeTlsStream};
 
@@ -287,6 +287,31 @@ impl Connection {
             None
         }
     }
+
+    pub fn deregister(&mut self, poll: &mut Poll) -> ::std::io::Result<()> {
+        match &mut self.inner {
+            ConnectionInner::Established(established) => {
+                match &mut established.stream {
+                    Stream::TcpStream(ref mut stream) => {
+                        poll.registry().deregister(stream)
+                    },
+                    Stream::TlsStream(ref mut stream) => {
+                        poll.registry().deregister(stream.get_mut())
+                    },
+                }
+            },
+            ConnectionInner::InProgress(TlsHandshakeMachine { inner, ..}) => {
+                match inner {
+                    TlsHandshakeMachineInner::TcpStream(ref mut stream) => {
+                        poll.registry().deregister(stream)
+                    },
+                    TlsHandshakeMachineInner::TlsMidHandshake(ref mut mid_handshake) => {
+                        poll.registry().deregister(mid_handshake.get_mut())
+                    },
+                }
+            },
+        }
+    }
 }
 
 
diff --git a/aquatic_http/src/lib/network/mod.rs b/aquatic_http/src/lib/network/mod.rs
index 7f2ee3c..5aa2085 100644
--- a/aquatic_http/src/lib/network/mod.rs
+++ b/aquatic_http/src/lib/network/mod.rs
@@ -105,6 +105,7 @@ pub fn run_poll_loop(
                 handle_connection_read_event(
                     &config,
                     socket_worker_index,
+                    &mut poll,
                     &request_channel_sender,
                     &mut local_responses,
                     &mut connections,
@@ -116,6 +117,7 @@ pub fn run_poll_loop(
         if !(local_responses.is_empty() & (response_channel_receiver.is_empty())) {
             send_responses(
                 &config,
+                &mut poll,
                 &mut response_buffer,
                 local_responses.drain(..),
                 response_channel_receiver.try_iter(),
@@ -125,7 +127,7 @@ pub fn run_poll_loop(
 
         // Remove inactive connections, but not every iteration
         if iter_counter % CONNECTION_CLEAN_INTERVAL == 0 {
-            remove_inactive_connections(&mut connections);
+            remove_inactive_connections(&mut poll, &mut connections);
         }
 
         iter_counter = iter_counter.wrapping_add(1);
@@ -155,7 +157,7 @@ fn accept_new_streams(
                 let token = *poll_token_counter;
 
                 // Remove connection if it exists (which is unlikely)
-                connections.remove(&token);
+                remove_connection(poll, connections, poll_token_counter);
 
                 poll.registry()
                     .register(&mut stream, token, Interest::READABLE)
@@ -186,6 +188,7 @@ fn accept_new_streams(
 pub fn handle_connection_read_event(
     config: &Config,
     socket_worker_index: usize,
+    poll: &mut Poll,
     request_channel_sender: &RequestChannelSender,
     local_responses: &mut Vec<(ConnectionMeta, Response)>,
     connections: &mut ConnectionMap,
@@ -256,14 +259,14 @@ pub fn handle_connection_read_event(
                 Err(RequestReadError::StreamEnded) => {
                     ::log::debug!("stream ended");
             
-                    connections.remove(&poll_token);
+                    remove_connection(poll, connections, &poll_token);
 
                     break
                 },
                 Err(RequestReadError::Io(err)) => {
                     ::log::info!("error reading request (io): {}", err);
             
-                    connections.remove(&poll_token);
+                    remove_connection(poll, connections, &poll_token);
     
                     break; 
                 },
@@ -306,6 +309,7 @@ pub fn handle_connection_read_event(
 /// Read responses from channel, send to peers
 pub fn send_responses(
     config: &Config,
+    poll: &mut Poll,
     buffer: &mut Cursor<&mut [u8]>,
     local_responses: Drain<(ConnectionMeta, Response)>,
     channel_responses: crossbeam_channel::TryIter<(ConnectionMeta, Response)>,
@@ -330,7 +334,7 @@ pub fn send_responses(
                     debug!("sent response");
 
                     if !config.network.keep_alive {
-                        connections.remove(&meta.poll_token);
+                        remove_connection(poll, connections, &meta.poll_token);
                     }
                 },
                 Err(err) if err.kind() == ErrorKind::WouldBlock => {
@@ -339,7 +343,7 @@ pub fn send_responses(
                 Err(err) => {
                     info!("error sending response: {}", err);
 
-                    connections.remove(&meta.poll_token);
+                    remove_connection(poll, connections, &meta.poll_token);
                 },
             }
         }
@@ -349,13 +353,35 @@ pub fn send_responses(
 
 // Close and remove inactive connections
 pub fn remove_inactive_connections(
+    poll: &mut Poll,
     connections: &mut ConnectionMap,
 ){
     let now = Instant::now();
 
     connections.retain(|_, connection| {
-        connection.valid_until.0 >= now
+        let keep = connection.valid_until.0 >= now;
+
+        if !keep {
+            if let Err(err) = connection.deregister(poll){
+                ::log::error!("deregister connection error: {}", err);
+            }
+        }
+
+        keep
     });
 
     connections.shrink_to_fit();
 }
+
+
+fn remove_connection(
+    poll: &mut Poll,
+    connections: &mut ConnectionMap,
+    connection_token: &Token,
+){
+    if let Some(mut connection) = connections.remove(connection_token){
+        if let Err(err) = connection.deregister(poll){
+            ::log::error!("deregister connection error: {}", err);
+        }
+    }
+}
\ No newline at end of file