diff --git a/docs/pages/connect-your-client/teleport-clients/teleport-connect.mdx b/docs/pages/connect-your-client/teleport-clients/teleport-connect.mdx
index af6e847d3e8e1..7878f127ce6fd 100644
--- a/docs/pages/connect-your-client/teleport-clients/teleport-connect.mdx
+++ b/docs/pages/connect-your-client/teleport-clients/teleport-connect.mdx
@@ -49,6 +49,15 @@ To choose the mode explicitly, add `/allusers` (per-machine) or `/currentuser` (
 $ "Teleport Connect Setup-(=teleport.version=).exe" /S /allusers
 ```
 
+<Admonition
+    type="warning"
+    title="Avoid Dual Installations"
+>
+  Having both per-user and per-machine installations may cause the Start Menu shortcut to point to a different instance than expected.
+
+  Before installing the app in a different mode, [uninstall](#uninstalling-teleport-connect) the existing installation.
+</Admonition>
+
 </TabItem>
 </Tabs>
 
diff --git a/docs/pages/includes/uninstall-teleport-connect-windows.mdx b/docs/pages/includes/uninstall-teleport-connect-windows.mdx
index 806450d223dee..521fc982f2c61 100644
--- a/docs/pages/includes/uninstall-teleport-connect-windows.mdx
+++ b/docs/pages/includes/uninstall-teleport-connect-windows.mdx
@@ -1,5 +1,14 @@
-  You can uninstall Teleport Connect from the "Apps and Features" section of the Control Panel.
+You can uninstall Teleport Connect from the "Programs and Features" section of the Control Panel.
 
-  For reference, Teleport Connect binaries are installed to:
-  * Per-machine install (default): `%PROGRAMFILES%\Teleport Connect`
-  * Per-user install: `%LOCALAPPDATA%\Teleport Connect`
+For reference, Teleport Connect binaries are installed to:
+* Per-machine install (default): `%PROGRAMFILES%\Teleport Connect`
+* Per-user install: `%LOCALAPPDATA%\Programs\Teleport Connect`
+
+To silently uninstall the app, open the Command Prompt and type:
+```code
+# For per-machine install (default):
+$ "%PROGRAMFILES%\Teleport Connect\Uninstall Teleport Connect.exe" /S /allusers
+
+# For per-user install:
+$ "%LOCALAPPDATA%\Programs\Teleport Connect\Uninstall Teleport Connect.exe" /S /currentuser
+````
diff --git a/web/packages/teleterm/src/ui/Vnet/VnetSliderStep.tsx b/web/packages/teleterm/src/ui/Vnet/VnetSliderStep.tsx
index d99b6e5d149f4..1f692c04e4b45 100644
--- a/web/packages/teleterm/src/ui/Vnet/VnetSliderStep.tsx
+++ b/web/packages/teleterm/src/ui/Vnet/VnetSliderStep.tsx
@@ -95,9 +95,9 @@ export const VnetSliderStep = (props: StepComponentProps) => {
               'missing-windows-service' && (
               <ErrorText>
                 VNet system service is not installed. <br />
-                To use VNet, reinstall Teleport Connect selecting &apos;Anyone
-                who uses this computer&apos; option. Administrator privileges
-                will be required.
+                To use VNet, uninstall Teleport Connect and install it again
+                selecting &apos;Anyone who uses this computer&apos; option.
+                Administrator privileges will be required.
               </ErrorText>
             )}
             {installTimeRequirementsCheck.reason.kind ===
@@ -106,9 +106,10 @@ export const VnetSliderStep = (props: StepComponentProps) => {
                 The VNet system service version does not match the application
                 version. <br />
                 This can happen if Teleport Connect is installed both per-user
-                and per-machine. To use VNet, reinstall Teleport Connect
-                selecting &apos;Anyone who uses this computer&apos; option.
-                Administrator privileges will be required.
+                and per-machine. To use VNet, uninstall both Teleport Connect
+                installations and install it again selecting &apos;Anyone who
+                uses this computer&apos; option. Administrator privileges will
+                be required.
               </ErrorText>
             )}
             {installTimeRequirementsCheck.reason.kind === 'error' && (