diff --git a/src/plugins/debugger/debuggertooltipmanager.cpp b/src/plugins/debugger/debuggertooltipmanager.cpp
index 5855b03366a..c4fe34872de 100644
--- a/src/plugins/debugger/debuggertooltipmanager.cpp
+++ b/src/plugins/debugger/debuggertooltipmanager.cpp
@@ -691,6 +691,13 @@ bool DebuggerToolTipContext::isSame(const DebuggerToolTipContext &other) const
             && iname == other.iname;
 }
 
+void DebuggerToolTipContext::appendFormatRequest(DebuggerCommand *cmd) const
+{
+    cmd->arg("expression", expression);
+    cmd->arg("fileName", fileName);
+    cmd->arg("iname", iname);
+}
+
 QString DebuggerToolTipContext::toolTip() const
 {
     return DebuggerToolTipManager::tr("Expression %1 in function %2 from line %3 to %4")
@@ -787,7 +794,10 @@ void DebuggerToolTipHolder::updateTooltip(DebuggerEngine *engine)
 
     StackFrame frame = engine->stackHandler()->currentFrame();
 
-    const bool sameFrame = context.matchesFrame(frame);
+    // FIXME: The engine should decide on whether it likes
+    // the context.
+    const bool sameFrame = context.matchesFrame(frame)
+        || context.fileName.endsWith(QLatin1String(".py"));
     DEBUG("UPDATE TOOLTIP: STATE " << state << context.iname
           << "PINNED: " << widget->isPinned
           << "SHOW NEEDED: " << widget->isPinned
diff --git a/src/plugins/debugger/debuggertooltipmanager.h b/src/plugins/debugger/debuggertooltipmanager.h
index 0538c8089a6..3174006c5e9 100644
--- a/src/plugins/debugger/debuggertooltipmanager.h
+++ b/src/plugins/debugger/debuggertooltipmanager.h
@@ -45,6 +45,7 @@ namespace Debugger {
 namespace Internal {
 
 class DebuggerEngine;
+class DebuggerCommand;
 class StackFrame;
 
 class DebuggerToolTipContext
@@ -54,6 +55,7 @@ public:
     bool isValid() const { return !expression.isEmpty(); }
     bool matchesFrame(const StackFrame &frame) const;
     bool isSame(const DebuggerToolTipContext &other) const;
+    void appendFormatRequest(DebuggerCommand *cmd) const;
     QString toolTip() const;
 
     QString fileName;
diff --git a/src/plugins/debugger/pdb/pdbengine.cpp b/src/plugins/debugger/pdb/pdbengine.cpp
index b3041de9424..5ac68dbb715 100644
--- a/src/plugins/debugger/pdb/pdbengine.cpp
+++ b/src/plugins/debugger/pdb/pdbengine.cpp
@@ -452,69 +452,16 @@ void PdbEngine::handleListSymbols(const DebuggerResponse &response, const QStrin
 //////////////////////////////////////////////////////////////////////
 
 
-static WatchData m_toolTip;
-static QPoint m_toolTipPos;
-
-bool PdbEngine::setToolTipExpression(TextEditor::TextEditorWidget *editorWidget,
+bool PdbEngine::setToolTipExpression(TextEditor::TextEditorWidget *,
     const DebuggerToolTipContext &ctx)
 {
-    if (state() != InferiorStopOk) {
-        //SDEBUG("SUPPRESSING DEBUGGER TOOLTIP, INFERIOR NOT STOPPED");
-        return false;
-    }
-    // Check mime type and get expression (borrowing some C++ - functions)
-    const QString javaPythonMimeType = QLatin1String("application/javascript");
-    if (editorWidget->textDocument()->mimeType() != javaPythonMimeType)
+    if (state() != InferiorStopOk)
         return false;
 
-    int line;
-    int column;
-    QString exp = cppExpressionAt(editorWidget, ctx.position, &line, &column);
-
-    QToolTip::hideText();
-    if (exp.isEmpty() || exp.startsWith(QLatin1Char('#')))  {
-        QToolTip::hideText();
-        return false;
-    }
-
-    if (!hasLetterOrNumber(exp)) {
-        QToolTip::showText(m_toolTipPos, tr("\"%1\" contains no identifier").arg(exp));
-        return true;
-    }
-
-    if (exp.startsWith(QLatin1Char('"')) && exp.endsWith(QLatin1Char('"'))) {
-        QToolTip::showText(m_toolTipPos, tr("String literal %1").arg(exp));
-        return true;
-    }
-
-    if (exp.startsWith(QLatin1String("++")) || exp.startsWith(QLatin1String("--")))
-        exp.remove(0, 2);
-
-    if (exp.endsWith(QLatin1String("++")) || exp.endsWith(QLatin1String("--")))
-        exp.remove(0, 2);
-
-    if (exp.startsWith(QLatin1Char('<')) || exp.startsWith(QLatin1Char('[')))
-        return false;
-
-    if (hasSideEffects(exp)) {
-        QToolTip::showText(m_toolTipPos,
-            tr("Cowardly refusing to evaluate expression \"%1\" "
-               "with potential side effects").arg(exp));
-        return true;
-    }
-
-#if 0
-    //if (status() != InferiorStopOk)
-    //    return;
-
-    // FIXME: 'exp' can contain illegal characters
-    m_toolTip = WatchData();
-    m_toolTip.exp = exp;
-    m_toolTip.name = exp;
-    m_toolTip.iname = tooltipIName;
-    insertData(m_toolTip);
-#endif
-    return false;
+    DebuggerCommand cmd("evaluateTooltip");
+    ctx.appendFormatRequest(&cmd);
+    runCommand(cmd);
+    return true;
 }
 
 
diff --git a/src/plugins/debugger/pdb/pdbengine.h b/src/plugins/debugger/pdb/pdbengine.h
index de99e6f03ec..bfd565f36b4 100644
--- a/src/plugins/debugger/pdb/pdbengine.h
+++ b/src/plugins/debugger/pdb/pdbengine.h
@@ -72,7 +72,7 @@ private:
     void shutdownInferior();
     void shutdownEngine();
 
-    bool setToolTipExpression(TextEditor::TextEditorWidget *editorWidget,
+    bool setToolTipExpression(TextEditor::TextEditorWidget *,
         const DebuggerToolTipContext &);
 
     void continueInferior();