diff --git a/python/pluginResources/messages/PyBundle.properties b/python/pluginResources/messages/PyBundle.properties
index 3b5e11fedc00..0b2bfe674c23 100644
--- a/python/pluginResources/messages/PyBundle.properties
+++ b/python/pluginResources/messages/PyBundle.properties
@@ -934,6 +934,7 @@ debugger.backend.debugpy.description=Python debugger backend built on the Debug
 debugger.backend.debugpy.disabled.tooltip=debugpy requires Python 3.9 or later
 debugger.backend.debugpy.disabled.remote.tooltip=debugpy is not supported for remote Python interpreters
 debugger.backend.debugpy.disabled.not.installed.tooltip=Install the Python DAP Debugger plugin to use the debugpy backend
+debugger.backend.debugpy.disabled.not.enabled.tooltip=Enable the Python DAP Debugger plugin to use the debugpy backend
 debugger.backend.install.debugpy.plugin=Install Python DAP Debugger Plugin
 debugger.backend.enable.debugpy.plugin=Enable Python DAP Debugger Plugin
 debugger.backend.report.issue.debugpy=Report an Issue with debugpy
@@ -1625,6 +1626,7 @@ advertiser.python.dap.plugin.enable.text=Enable Plugin
 
 debugger.dap.plugin.install.got.it.header=Try the Python DAP Debugger plugin
 debugger.dap.plugin.install.got.it.text=Install the Python DAP Debugger plugin for faster and more reliable Python debugging with debugpy
+debugger.dap.plugin.enable.got.it.text=Enable the Python DAP Debugger plugin for faster and more reliable Python debugging with debugpy
 
 action.PyInstallPackage.text=Install
 action.PyInstallPackageAction.text=Advanced Package Install\u2026
diff --git a/python/src/com/jetbrains/python/debugger/PyDapPluginInstallGotItListener.kt b/python/src/com/jetbrains/python/debugger/PyDapPluginInstallGotItListener.kt
index 60d0ddebe43f..d47b7d63a8ed 100644
--- a/python/src/com/jetbrains/python/debugger/PyDapPluginInstallGotItListener.kt
+++ b/python/src/com/jetbrains/python/debugger/PyDapPluginInstallGotItListener.kt
@@ -40,8 +40,13 @@ internal class PyDapPluginInstallGotItListener : XDebuggerManagerListener {
     if (isAcked()) return
 
     val project = session.project
-    val builder = GotItComponentBuilder { PyBundle.message("debugger.dap.plugin.install.got.it.text") }
-      .withHeader(PyBundle.message("debugger.dap.plugin.install.got.it.header"))
+    // Resolved lazily: the tooltip can appear up to 30 seconds later, and the plugin may be enabled meanwhile.
+    val builder = GotItComponentBuilder {
+      PyBundle.message(
+        if (isPythonDapPluginInstalledButDisabled()) "debugger.dap.plugin.enable.got.it.text"
+        else "debugger.dap.plugin.install.got.it.text"
+      )
+    }.withHeader(PyBundle.message("debugger.dap.plugin.install.got.it.header"))
     showGotItWhenContentSelected(session, builder) {
       findBackendSwitcherButton(project)
     }
diff --git a/python/src/com/jetbrains/python/debugger/PyDebuggerBackendSwitcherAction.kt b/python/src/com/jetbrains/python/debugger/PyDebuggerBackendSwitcherAction.kt
index a974244339e6..b3df875495a7 100644
--- a/python/src/com/jetbrains/python/debugger/PyDebuggerBackendSwitcherAction.kt
+++ b/python/src/com/jetbrains/python/debugger/PyDebuggerBackendSwitcherAction.kt
@@ -166,16 +166,17 @@ internal class PyDebuggerBackendSwitcherAction : ComboBoxAction(), DumbAware {
       if (backend == PyDebuggerBackend.DEBUGPY && !isDebugpyAvailableInProject(project)) {
         e.presentation.isEnabled = false
         @Suppress("DialogTitleCapitalization")
-        val disabledMsg = if (!isPythonDapPluginInstalledAndEnabled()) {
-          PyBundle.message("debugger.backend.debugpy.disabled.not.installed.tooltip")
-        }
-        else {
-          val sdk = getEffectiveSdk(project)
-          if (sdk != null && PythonSdkUtil.isRemote(sdk)) {
-            PyBundle.message("debugger.backend.debugpy.disabled.remote.tooltip")
-          }
-          else {
-            PyBundle.message("debugger.backend.debugpy.disabled.tooltip")
+        val disabledMsg = when {
+          isPythonDapPluginInstalledButDisabled() -> PyBundle.message("debugger.backend.debugpy.disabled.not.enabled.tooltip")
+          !isPythonDapPluginInstalledAndEnabled() -> PyBundle.message("debugger.backend.debugpy.disabled.not.installed.tooltip")
+          else -> {
+            val sdk = getEffectiveSdk(project)
+            if (sdk != null && PythonSdkUtil.isRemote(sdk)) {
+              PyBundle.message("debugger.backend.debugpy.disabled.remote.tooltip")
+            }
+            else {
+              PyBundle.message("debugger.backend.debugpy.disabled.tooltip")
+            }
           }
         }
         e.presentation.description = disabledMsg