diff --git a/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js b/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js
index 61e1ed6c..1787dc62 100644
--- a/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js
+++ b/src/octoprint/plugins/pluginmanager/static/js/pluginmanager.js
@@ -646,6 +646,7 @@ $(function() {
 
             self.loglines.removeAll();
             self.loglines.push({line: line, stream: "message"});
+            self._scrollWorkingOutputToEnd();
 
             self.workingDialog.modal("show");
         };
@@ -746,7 +747,7 @@ $(function() {
 
             if (messageType == "loglines" && self.working()) {
                 _.each(data.loglines, function(line) {
-                    self.loglines.push(line);
+                    self.loglines.push(self._preprocessLine(line));
                 });
                 self._scrollWorkingOutputToEnd();
             } else if (messageType == "result") {
@@ -861,6 +862,14 @@ $(function() {
                 self.requestData();
             }
         };
+
+        self._forcedStdoutLine = /You are using pip version .*?, however version .*? is available\.|You should consider upgrading via the '.*?' command\./;
+        self._preprocessLine = function(line) {
+            if (line.stream == "stderr" && line.line.match(self._forcedStdoutLine)) {
+                line.stream = "stdout";
+            }
+            return line;
+        }
     }
 
     // view model class, parameters for constructor, container to bind to
diff --git a/src/octoprint/plugins/softwareupdate/static/js/softwareupdate.js b/src/octoprint/plugins/softwareupdate/static/js/softwareupdate.js
index 294c65d4..c9234e0b 100644
--- a/src/octoprint/plugins/softwareupdate/static/js/softwareupdate.js
+++ b/src/octoprint/plugins/softwareupdate/static/js/softwareupdate.js
@@ -539,7 +539,7 @@ $(function() {
                 case "loglines": {
                     if (self.working()) {
                         _.each(messageData.loglines, function(line) {
-                            self.loglines.push(line);
+                            self.loglines.push(self._preprocessLine(line));
                         });
                         self._scrollWorkingOutputToEnd();
                     }
@@ -557,6 +557,7 @@ $(function() {
                     self.loglines.push({line: _.repeat("+", text.length), stream: "separator"});
                     self.loglines.push({line: text, stream: "message"});
                     self.loglines.push({line: _.repeat("+", text.length), stream: "separator"});
+                    self._scrollWorkingOutputToEnd();
                     self._updatePopup({
                         text: text,
                         hide: false,
@@ -584,6 +585,7 @@ $(function() {
                     };
 
                     self.loglines.push({line: text, stream: "message"});
+                    self._scrollWorkingOutputToEnd();
 
                     self.waitingForRestart = true;
                     self.restartTimeout = setTimeout(function() {
@@ -694,6 +696,13 @@ $(function() {
             }
         };
 
+        self._forcedStdoutLine = /You are using pip version .*?, however version .*? is available\.|You should consider upgrading via the '.*?' command\./;
+        self._preprocessLine = function(line) {
+            if (line.stream == "stderr" && line.line.match(self._forcedStdoutLine)) {
+                line.stream = "stdout";
+            }
+            return line;
+        }
     }
 
     // view model class, parameters for constructor, container to bind to