From 66e71d570ba03748a61030f438ee1384cd400d3e Mon Sep 17 00:00:00 2001
From: EdwardAngert <17991901+EdwardAngert@users.noreply.github.com>
Date: Mon, 14 Jul 2025 14:54:19 +0000
Subject: [PATCH 1/4] macos vpn issue

---
 docs/user-guides/desktop/index.md | 26 +++++++++++++++++++++++++-
 1 file changed, 25 insertions(+), 1 deletion(-)

diff --git a/docs/user-guides/desktop/index.md b/docs/user-guides/desktop/index.md
index d47c2d2a604de..872c4146a8ea5 100644
--- a/docs/user-guides/desktop/index.md
+++ b/docs/user-guides/desktop/index.md
@@ -14,6 +14,12 @@ You can install Coder Desktop on macOS or Windows.
 
 ### macOS
 
+> [!IMPORTANT]
+> Coder Desktop can't connect through another VPN.
+>
+> Due to a [known issue](#mac-coder-desktop-cant-connect-through-another-vpn),
+> if your Coder deployment is requires that you connect through a VPN, Desktop will timeout when it tries to connect.
+
 1. Use [Homebrew](https://brew.sh/) to install Coder Desktop:
 
    ```shell
@@ -121,7 +127,25 @@ Before you can use Coder Desktop, you will need to sign in.
 
 ## Troubleshooting
 
-Do not install more than one copy of Coder Desktop. To avoid system VPN configuration conflicts, only one copy of `Coder Desktop.app` should exist on your Mac, and it must remain in `/Applications`.
+If you encounter an issue with Coder Desktop that is not listed here, file an issue in the GitHub repository for
+Coder Desktop for [macOS](https://github.com/coder/coder-desktop-macos/issues) or
+[Windows](https://github.com/coder/coder-desktop-windows/issues), in the
+[main Coder repository](https://github.com/coder/coder/issues), or consult the
+[community on Discord](https://coder.com/chat).
+
+### Known Issues
+
+#### Do not install more than one copy of Coder Desktop
+
+To avoid system VPN configuration conflicts, only one copy of `Coder Desktop.app` should exist on your Mac, and it must remain in `/Applications`.
+
+#### macOS: Coder Desktop can't connect through another VPN
+
+If the logged in Coder deployment requires a VPN to connect, Coder Connect can't establish communication through the VPN,
+and will time out.
+
+This is due to a [known issue](https://github.com/coder/coder-desktop-macos/issues/201) with how macOS network extensions
+communicate with each other and a resolution is in progress.
 
 ## Next Steps
 

From 5c38c7b75466a32c89ac857ac335b36459c9edcc Mon Sep 17 00:00:00 2001
From: EdwardAngert <17991901+EdwardAngert@users.noreply.github.com>
Date: Mon, 14 Jul 2025 15:01:21 +0000
Subject: [PATCH 2/4] windows vpn issue too

---
 docs/user-guides/desktop/index.md | 28 +++++++++++++++-------------
 1 file changed, 15 insertions(+), 13 deletions(-)

diff --git a/docs/user-guides/desktop/index.md b/docs/user-guides/desktop/index.md
index 872c4146a8ea5..6234a0e61c13d 100644
--- a/docs/user-guides/desktop/index.md
+++ b/docs/user-guides/desktop/index.md
@@ -1,25 +1,25 @@
 # Coder Desktop
 
 Coder Desktop provides seamless access to your remote workspaces without the need to install a CLI or configure manual port forwarding.
-Connect to workspace services using simple hostnames like `myworkspace.coder`, launch native applications with one click, and synchronize files between local and remote environments.
+Connect to workspace services using simple hostnames like `myworkspace.coder`, launch native applications with one click,
+and synchronize files between local and remote environments.
 
-> [!NOTE]
-> Coder Desktop requires a Coder deployment running [v2.20.0](https://github.com/coder/coder/releases/tag/v2.20.0) or later.
+Coder Desktop requires a Coder deployment running [v2.20.0](https://github.com/coder/coder/releases/tag/v2.20.0) or later.
 
 ## Install Coder Desktop
 
+> [!IMPORTANT]
+> Coder Desktop can't connect through another VPN.
+>
+> Due to a [known issue](#coder-desktop-cant-connect-through-another-vpn),
+> if your Coder deployment is requires that you connect through a VPN, Desktop will timeout when it tries to connect.
+
 <div class="tabs">
 
 You can install Coder Desktop on macOS or Windows.
 
 ### macOS
 
-> [!IMPORTANT]
-> Coder Desktop can't connect through another VPN.
->
-> Due to a [known issue](#mac-coder-desktop-cant-connect-through-another-vpn),
-> if your Coder deployment is requires that you connect through a VPN, Desktop will timeout when it tries to connect.
-
 1. Use [Homebrew](https://brew.sh/) to install Coder Desktop:
 
    ```shell
@@ -135,17 +135,19 @@ Coder Desktop for [macOS](https://github.com/coder/coder-desktop-macos/issues) o
 
 ### Known Issues
 
-#### Do not install more than one copy of Coder Desktop
+#### macOS: Do not install more than one copy of Coder Desktop
 
 To avoid system VPN configuration conflicts, only one copy of `Coder Desktop.app` should exist on your Mac, and it must remain in `/Applications`.
 
-#### macOS: Coder Desktop can't connect through another VPN
+#### Coder Desktop can't connect through another VPN
 
 If the logged in Coder deployment requires a VPN to connect, Coder Connect can't establish communication through the VPN,
 and will time out.
 
-This is due to a [known issue](https://github.com/coder/coder-desktop-macos/issues/201) with how macOS network extensions
-communicate with each other and a resolution is in progress.
+This is due to known issues with how [macOS](https://github.com/coder/coder-desktop-macos/issues/201) and
+[Windows](https://github.com/coder/coder-desktop-windows/issues/147)
+network extensions communicate with each other.
+A resolution is in progress.
 
 ## Next Steps
 

From 1f840100dd5750dce124fdd2e73b8374cc5e839c Mon Sep 17 00:00:00 2001
From: Edward Angert <EdwardAngert@users.noreply.github.com>
Date: Mon, 14 Jul 2025 11:18:36 -0400
Subject: [PATCH 3/4] Update docs/user-guides/desktop/index.md

Co-authored-by: Dean Sheather <dean@deansheather.com>
---
 docs/user-guides/desktop/index.md | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/docs/user-guides/desktop/index.md b/docs/user-guides/desktop/index.md
index 6234a0e61c13d..7bb5d7d362ac8 100644
--- a/docs/user-guides/desktop/index.md
+++ b/docs/user-guides/desktop/index.md
@@ -12,7 +12,7 @@ Coder Desktop requires a Coder deployment running [v2.20.0](https://github.com/c
 > Coder Desktop can't connect through another VPN.
 >
 > Due to a [known issue](#coder-desktop-cant-connect-through-another-vpn),
-> if your Coder deployment is requires that you connect through a VPN, Desktop will timeout when it tries to connect.
+> if your Coder deployment requires that you connect through a corporate VPN, Desktop will timeout when it tries to connect.
 
 <div class="tabs">
 

From 5cb39bbaff02dbff248eb75e83516fda658cf274 Mon Sep 17 00:00:00 2001
From: EdwardAngert <17991901+EdwardAngert@users.noreply.github.com>
Date: Mon, 14 Jul 2025 16:20:56 +0000
Subject: [PATCH 4/4] corp. vpn

---
 docs/user-guides/desktop/index.md | 13 ++++++-------
 1 file changed, 6 insertions(+), 7 deletions(-)

diff --git a/docs/user-guides/desktop/index.md b/docs/user-guides/desktop/index.md
index 7bb5d7d362ac8..116f7d4d6de69 100644
--- a/docs/user-guides/desktop/index.md
+++ b/docs/user-guides/desktop/index.md
@@ -9,7 +9,7 @@ Coder Desktop requires a Coder deployment running [v2.20.0](https://github.com/c
 ## Install Coder Desktop
 
 > [!IMPORTANT]
-> Coder Desktop can't connect through another VPN.
+> Coder Desktop can't connect through a corporate VPN.
 >
 > Due to a [known issue](#coder-desktop-cant-connect-through-another-vpn),
 > if your Coder deployment requires that you connect through a corporate VPN, Desktop will timeout when it tries to connect.
@@ -119,7 +119,7 @@ Before you can use Coder Desktop, you will need to sign in.
 
    ![Coder Desktop on Windows - enable Coder Connect](../../images/user-guides/desktop/coder-desktop-win-enable-coder-connect.png)
 
-   This may take a few moments, as Coder Desktop will download the necessary components from the Coder server if they have been updated.
+   This may take a few moments, because Coder Desktop will download the necessary components from the Coder server if they have been updated.
 
 1. macOS: You may be prompted to enter your password to allow Coder Connect to start.
 
@@ -141,12 +141,11 @@ To avoid system VPN configuration conflicts, only one copy of `Coder Desktop.app
 
 #### Coder Desktop can't connect through another VPN
 
-If the logged in Coder deployment requires a VPN to connect, Coder Connect can't establish communication through the VPN,
-and will time out.
+If the logged in Coder deployment requires a corporate VPN to connect, Coder Connect can't establish communication
+through the VPN, and will time out.
 
-This is due to known issues with how [macOS](https://github.com/coder/coder-desktop-macos/issues/201) and
-[Windows](https://github.com/coder/coder-desktop-windows/issues/147)
-network extensions communicate with each other.
+This is due to known issues with [macOS](https://github.com/coder/coder-desktop-macos/issues/201) and
+[Windows](https://github.com/coder/coder-desktop-windows/issues/147) networking.
 A resolution is in progress.
 
 ## Next Steps

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