diff --git a/cli/root.go b/cli/root.go
index fe6d5c4ccd8a9..5a3c20a6e5ee1 100644
--- a/cli/root.go
+++ b/cli/root.go
@@ -1366,7 +1366,7 @@ func defaultUpgradeMessage(version string) string {
 	// to the GitHub release page to download the latest installer.
 	version = strings.TrimPrefix(version, "v")
 	if runtime.GOOS == "windows" {
-		return fmt.Sprintf("download the server version from: https://github.com/coder/coder/releases/v%s", version)
+		return ""
 	}
 	return fmt.Sprintf("download the server version with: 'curl -L https://coder.com/install.sh | sh -s -- --version %s'", version)
 }
@@ -1412,8 +1412,8 @@ func wrapTransportWithVersionMismatchCheck(rt http.RoundTripper, inv *serpent.In
 				switch {
 				case serverInfo.UpgradeMessage != "":
 					upgradeMessage = serverInfo.UpgradeMessage
-				// The site-local `install.sh` was introduced in v2.19.0
-				case serverInfo.DashboardURL != "" && semver.Compare(semver.MajorMinor(serverVersion), "v2.19") >= 0:
+				// The site-local `install.sh` was introduced in v2.19.0. Skip curl instruction on Windows.
+				case runtime.GOOS != "windows" && serverInfo.DashboardURL != "" && semver.Compare(semver.MajorMinor(serverVersion), "v2.19") >= 0:
 					upgradeMessage = fmt.Sprintf("download %s with: 'curl -fsSL %s/install.sh | sh'", serverVersion, serverInfo.DashboardURL)
 				}
 			}