diff --git a/openpype/tools/pyblish_pype/app.py b/openpype/tools/pyblish_pype/app.py
index d15d586103..a252b96427 100644
--- a/openpype/tools/pyblish_pype/app.py
+++ b/openpype/tools/pyblish_pype/app.py
@@ -90,9 +90,8 @@ def show(parent=None):
         install_fonts()
         install_translator(app)
 
-        ctrl = control.Controller()
-
         if self._window is None:
+            ctrl = control.Controller()
             self._window = window.Window(ctrl, parent)
             self._window.destroyed.connect(on_destroyed)
 
diff --git a/openpype/tools/pyblish_pype/control.py b/openpype/tools/pyblish_pype/control.py
index 455a338499..6f89952c22 100644
--- a/openpype/tools/pyblish_pype/control.py
+++ b/openpype/tools/pyblish_pype/control.py
@@ -228,6 +228,16 @@ class Controller(QtCore.QObject):
     def reset_context(self):
         self.log.debug("Resetting pyblish context object")
 
+        comment = None
+        if (
+            self.context is not None and
+            self.context.data.get("comment") and
+            # We only preserve the user typed comment if we are *not*
+            # resetting from a successful publish without errors
+            self._current_state != "Published"
+        ):
+            comment = self.context.data["comment"]
+
         self.context = pyblish.api.Context()
 
         self.context._publish_states = InstanceStates.ContextType
@@ -249,6 +259,10 @@ class Controller(QtCore.QObject):
 
         self.context.families = ("__context__",)
 
+        if comment:
+            # Preserve comment on reset if user previously had a comment
+            self.context.data["comment"] = comment
+
         self.log.debug("Reset of pyblish context object done")
 
     def reset(self):
diff --git a/openpype/tools/pyblish_pype/window.py b/openpype/tools/pyblish_pype/window.py
index 38907c1a52..d27ec34345 100644
--- a/openpype/tools/pyblish_pype/window.py
+++ b/openpype/tools/pyblish_pype/window.py
@@ -1139,9 +1139,10 @@ class Window(QtWidgets.QDialog):
             self.intent_box.setCurrentIndex(self.intent_model.default_index)
 
         self.comment_box.placeholder.setVisible(False)
-        self.comment_box.placeholder.setVisible(True)
         # Launch controller reset
         self.controller.reset()
+        if not self.comment_box.text():
+            self.comment_box.placeholder.setVisible(True)
 
     def validate(self):
         self.info(self.tr("Preparing validate.."))