diff --git a/autoload/vimspector/internal/channel.vim b/autoload/vimspector/internal/channel.vim
index eb7cc9d..c58ff64 100644
--- a/autoload/vimspector/internal/channel.vim
+++ b/autoload/vimspector/internal/channel.vim
@@ -42,6 +42,12 @@ function! s:_Send( msg ) abort
   call ch_sendraw( s:ch, a:msg )
 endfunction
 
+function! vimspector#internal#channel#Timeout( id ) abort
+  py3 << EOF
+_vimspector_session.OnRequestTimeout( vim.eval( 'a:id' ) )
+EOF
+endfunction
+
 function! vimspector#internal#channel#StartDebugSession( config ) abort
 
   if exists( 's:ch' )
diff --git a/autoload/vimspector/internal/job.vim b/autoload/vimspector/internal/job.vim
index d252629..68aa58e 100644
--- a/autoload/vimspector/internal/job.vim
+++ b/autoload/vimspector/internal/job.vim
@@ -55,7 +55,7 @@ endfunction
 
 function! vimspector#internal#job#StartDebugSession( config ) abort
   if exists( 's:job' )
-    echo "Job is already running"
+    echom "Job is already running"
     return v:none
   endif
 
@@ -81,6 +81,10 @@ function! vimspector#internal#job#StartDebugSession( config ) abort
 endfunction
 
 function! vimspector#internal#job#StopDebugSession() abort
+  if ! exists( 's:job' )
+    return
+  endfunction
+
   if job_status( s:job ) == 'run'
     call job_stop( s:job, 'term' )
   endif
diff --git a/python3/vimspector/debug_adapter_connection.py b/python3/vimspector/debug_adapter_connection.py
index 1932b5c..0cddf80 100644
--- a/python3/vimspector/debug_adapter_connection.py
+++ b/python3/vimspector/debug_adapter_connection.py
@@ -15,13 +15,17 @@
 
 import logging
 import json
-
-from collections import namedtuple
+import vim
 
 from vimspector import utils
 
-PendingRequest = namedtuple( 'PendingRequest',
-                             [ 'msg', 'handler', 'failure_handler' ] )
+
+class PendingRequest( object ):
+  def __init__( self, msg, handler, failure_handler, expiry_id ):
+    self.msg = msg
+    self.handler = handler
+    self.failure_handler = failure_handler
+    self.expiry_id = expiry_id
 
 
 class DebugAdapterConnection( object ):
@@ -36,18 +40,40 @@ class DebugAdapterConnection( object ):
     self._next_message_id = 0
     self._outstanding_requests = {}
 
-  def DoRequest( self, handler, msg, failure_handler=None ):
+  def DoRequest( self,
+                 handler,
+                 msg,
+                 failure_handler=None,
+                 timeout = 5000 ):
     this_id = self._next_message_id
     self._next_message_id += 1
 
     msg[ 'seq' ] = this_id
     msg[ 'type' ] = 'request'
 
+    # TODO/FIXME: This is so messy
+    expiry_id = vim.eval(
+      'timer_start( {}, "vimspector#internal#channel#Timeout" )'.format(
+        timeout ) )
+
     self._outstanding_requests[ this_id ] = PendingRequest( msg,
                                                             handler,
-                                                            failure_handler )
+                                                            failure_handler,
+                                                            expiry_id )
     self._SendMessage( msg )
 
+  def OnRequestTimeout( self, timer_id ):
+    request_id = None
+    for seq, request in self._outstanding_requests.items():
+      if request.expiry_id == timer_id:
+        self._AbortRequest( request, 'Timeout' )
+        request_id = seq
+        break
+
+    # Avoid modifying _outstanding_requests while looping
+    if request_id is not None:
+      del self._outstanding_requests[ request_id ]
+
   def DoResponse( self, request, error, response ):
     this_id = self._next_message_id
     self._next_message_id += 1
@@ -69,6 +95,21 @@ class DebugAdapterConnection( object ):
   def Reset( self ):
     self._Write = None
     self._handler = None
+    for _, request in self._outstanding_requests.items():
+      self._AbortRequest( request, 'Closing down' )
+    self._outstanding_requests.clear()
+
+  def _AbortRequest( self, request, reason ):
+    self._logger.debug( 'Aborting request {} because {}'.format(
+      json.dumps( request.msg ),
+      reason ) )
+
+    _KillTimer( request )
+    if request.failure_handler:
+      request.failure_handler( reason, {} )
+    else:
+      utils.UserMessage( 'Request aborted: {}'.format( reason ) )
+
 
   def OnData( self, data ):
     data = bytes( data, 'utf-8' )
@@ -170,6 +211,8 @@ class DebugAdapterConnection( object ):
         self._logger.exception( 'Duplicate response: {}'.format( message ) )
         return
 
+      _KillTimer( request )
+
       if message[ 'success' ]:
         if request.handler:
           request.handler( message )
@@ -181,7 +224,7 @@ class DebugAdapterConnection( object ):
             # TODO: Actually make this work
             reason = fmt
           else:
-            message = 'No reason'
+            reason = 'No reason'
 
         self._logger.error( 'Request failed: {0}'.format( reason ) )
         if request.failure_handler:
@@ -203,3 +246,9 @@ class DebugAdapterConnection( object ):
         utils.UserMessage(
           'Unhandled request: {0}'.format( message[ 'command' ] ),
           persist = True )
+
+
+def _KillTimer( request ):
+  if request.expiry_id is not None:
+    vim.eval( 'timer_stop( {} )'.format( request.expiry_id ) )
+    request.expiry_id = None
diff --git a/python3/vimspector/debug_session.py b/python3/vimspector/debug_session.py
index f3b9cd0..1019b33 100644
--- a/python3/vimspector/debug_session.py
+++ b/python3/vimspector/debug_session.py
@@ -189,6 +189,10 @@ class DebugSession( object ):
     if self._connection:
       self._connection.OnData( data )
 
+  def OnRequestTimeout( self, timer_id ):
+    if self._connection:
+      self._connection.OnRequestTimeout( timer_id )
+
   def OnChannelClosed( self ):
     self._connection = None
 
@@ -384,7 +388,7 @@ class DebugSession( object ):
     # scope)
     state = { 'done': False }
 
-    def handler( self ):
+    def handler( *args ):
       state[ 'done' ] = True
 
     self._connection.DoRequest( handler, {
@@ -392,11 +396,10 @@ class DebugSession( object ):
       'arguments': {
         'terminateDebugee': True
       },
-    } )
+    }, failure_handler = handler )
 
-    tries = 0
-    while not state[ 'done' ] and tries < 10:
-      tries = tries + 1
+    # This request times out after 5 seconds
+    while not state[ 'done' ]:
       vim.eval( 'vimspector#internal#{}#ForceRead()'.format(
         self._connection_type ) )
 
@@ -404,7 +407,7 @@ class DebugSession( object ):
       self._connection_type ) )
 
   def _StopDebugAdapter( self, callback = None ):
-    def handler( message ):
+    def handler( *args ):
       vim.eval( 'vimspector#internal#{}#StopDebugSession()'.format(
         self._connection_type ) )
 
@@ -423,7 +426,7 @@ class DebugSession( object ):
       'arguments': {
         'terminateDebugee': True
       },
-    } )
+    }, failure_handler = handler )
 
   def _SelectProcess( self, adapter_config, launch_config ):
     atttach_config = adapter_config[ 'attach' ]