diff --git a/plugin/src/ApiContext.lua b/plugin/src/ApiContext.lua
index 31893647..44259c1c 100644
--- a/plugin/src/ApiContext.lua
+++ b/plugin/src/ApiContext.lua
@@ -82,11 +82,16 @@ function ApiContext.new(baseUrl)
 		__baseUrl = baseUrl,
 		__serverId = nil,
 		__messageCursor = -1,
+		__connected = true,
 	}
 
 	return setmetatable(self, ApiContext)
 end
 
+function ApiContext:disconnect()
+	self.__connected = false
+end
+
 function ApiContext:connect()
 	local url = ("%s/api/rojo"):format(self.__baseUrl)
 
@@ -132,7 +137,7 @@ function ApiContext:retrieveMessages()
 	local function sendRequest()
 		return Http.get(url)
 			:catch(function(err)
-				if err.type == Http.Error.Kind.Timeout then
+				if err.type == Http.Error.Kind.Timeout and self.__connected then
 					return sendRequest()
 				end
 
diff --git a/plugin/src/ServeSession.lua b/plugin/src/ServeSession.lua
index 8b6de64a..6033dde4 100644
--- a/plugin/src/ServeSession.lua
+++ b/plugin/src/ServeSession.lua
@@ -109,12 +109,17 @@ function ServeSession:start()
 				end)
 		end)
 		:catch(function(err)
-			self:__setStatus(Status.Disconnected, err)
+			self:__stopInternal(err)
 		end)
 end
 
 function ServeSession:stop()
-	self:__setStatus(Status.Disconnected)
+	self:__stopInternal()
+end
+
+function ServeSession:__stopInternal(err)
+	self:__setStatus(Status.Disconnected, err)
+	self.__apiContext:disconnect()
 end
 
 function ServeSession:__setStatus(status, detail)