 			$scope.pdf.view = 'errors'
 			$scope.pdf.renderingError = true
 
-		autoCompileTimeout = null
+		autoCompileInterval = null
+		autoCompileIfReady = () ->
+			if $scope.pdf.compiling
+				return
+
+			# Only checking linting if syntaxValidation is on and visible to the user
+			autoCompileLintingError = ide.$scope.hasLintingError and ide.$scope.settings.syntaxValidation
+			if $scope.autoCompileLintingError != autoCompileLintingError
+				$scope.$apply () ->
+					$scope.autoCompileLintingError = autoCompileLintingError
+					# We've likely been waiting a while until the user fixed the linting, but we
+					# don't want to compile as soon as it is fixed, so reset the timeout.
+					$scope.startedTryingAutoCompileAt = Date.now()
+					$scope.docLastChangedAt = Date.now()
+			if autoCompileLintingError
+				return
+
+			# If there's a longish compile, don't compile immediately after if user is still typing
+			startedTryingAt = Math.max($scope.startedTryingAutoCompileAt, $scope.lastFinishedCompileAt || 0)
+
+			timeSinceStartedTrying = Date.now() - startedTryingAt
+			timeSinceLastChange = Date.now() - $scope.docLastChangedAt
+
+			shouldCompile = false
+			if timeSinceLastChange > AUTO_COMPILE_DEBOUNCE # Don't compile in the middle of the user typing
+				shouldCompile = true
+			else if timeSinceStartedTrying > AUTO_COMPILE_MAX_WAIT # Unless they type for a long time
+				shouldCompile = true
+			else if timeSinceStartedTrying < 0 or timeSinceLastChange < 0
+				# If time is non-monotonic, assume that the user's system clock has been
+				# changed and continue with compile
+				shouldCompile = true
+
+			if shouldCompile
+				triggerAutoCompile()
+
 		triggerAutoCompile = () ->
-			return if autoCompileTimeout or $scope.ui.pdfHidden
-
-			timeSinceLastCompile = Date.now() - $scope.recompiledAt
-			# If time is non-monotonic, assume that the user's system clock has been
-			# changed and continue with recompile
-			isTimeNonMonotonic = timeSinceLastCompile < 0
-
-			if isTimeNonMonotonic || timeSinceLastCompile >= AUTO_COMPILE_TIMEOUT
-				# If user has code check disabled, it is likely because they have
-				# linting errors that they are ignoring. Therefore it doesn't make sense
-				# to block auto compiles. It also causes problems where server-provided
-				# linting errors aren't cleared after typing
-				if (ide.$scope.settings.syntaxValidation and !ide.$scope.hasLintingError)
-					$scope.recompile(isAutoCompileOnChange: true) # compile if no linting errors
-				else if !ide.$scope.settings.syntaxValidation
-					$scope.recompile(isAutoCompileOnChange: true) # always recompile
-				else
-					$scope.$apply () ->
-						$scope.autoCompileLintingError = true
+			$scope.recompile(isAutoCompileOnChange: true)
+
+		startTryingAutoCompile = () ->
+			return if autoCompileInterval?
+			$scope.startedTryingAutoCompileAt = Date.now()
+			autoCompileInterval = setInterval autoCompileIfReady, 200
+
+		stopTryingAutoCompile = () ->
+			clearInterval autoCompileInterval
+			autoCompileInterval = null
+
+		$scope.$watch "uncompiledChanges", (uncompiledChanges) ->
+			if uncompiledChanges
+				startTryingAutoCompile()
 			else
-				# Extend remainder of timeout
-				autoCompileTimeout = setTimeout () ->
-					autoCompileTimeout = null
-					triggerAutoCompile()
-				, AUTO_COMPILE_TIMEOUT - timeSinceLastCompile
+				stopTryingAutoCompile()
 
 		$scope.uncompiledChanges = false
 		recalculateUncompiledChanges = () ->
-			if $scope.docLastChanged > $scope.projectLastCompiled
+			if $scope.ui.pdfHidden
+				# Don't both auto-compiling if pdf isn't visible
+				$scope.uncompiledChanges = false
+			else if !$scope.docLastChangedAt?
+				$scope.uncompiledChanges = false
+			else if !$scope.lastStartedCompileAt? or $scope.docLastChangedAt > $scope.lastStartedCompileAt
 				$scope.uncompiledChanges = true
 			else
 				$scope.uncompiledChanges = false
 
+		_updateDocLastChangedAt = () ->
+			$scope.docLastChangedAt = Date.now()
+			recalculateUncompiledChanges()
+
 		onDocChanged = () ->
 			$scope.autoCompileLintingError = false
-			$scope.docLastChanged = Date.now()
+			_updateDocLastChangedAt()
+
+		onDocSaved = () ->
+			# We use the save as a trigger too, to account for the delay between the client
+			# and server. Otherwise, we might have compiled after the user made
+			# the change on the client, but before the server had it.
+			_updateDocLastChangedAt()
+
+		onCompilingStateChanged = (compiling) ->
 			recalculateUncompiledChanges()
-
-		onCompilingStateChanged = (compiling) ->
-			if compiling
-				$scope.projectLastCompiled = Date.now()
-				recalculateUncompiledChanges()
 
 		autoCompileListeners = []
 		toggleAutoCompile = (enabling) ->
 			if enabling
 				autoCompileListeners = [
 					ide.$scope.$on "doc:changed", onDocChanged
-					ide.$scope.$on "doc:saved", onDocChanged
+					ide.$scope.$on "doc:saved", onDocSaved
 					$scope.$watch "pdf.compiling", onCompilingStateChanged
-					ide.$scope.$on "ide:opAcknowledged", _.debounce(triggerAutoCompile, OP_ACKNOWLEDGEMENT_TIMEOUT)
 				]
 			else
 				for unbind in autoCompileListeners

					$scope.pdf.error = true
					$scope.pdf.view = 'errors'
				.finally () ->
					$scope.recompiledAt = Date.now()

		# This needs to be public.
		ide.$scope.recompile = $scope.recompile

			ide.$scope.$broadcast("flush-changes")

			options.rootDocOverride_id = getRootDocOverride_id()

			$scope.$apply()

			sendCompileRequest(options)
				.then (response) ->
