diff --git a/cmd/derper/depaware.txt b/cmd/derper/depaware.txt
index a776c4cb3..58c5e26ac 100644
--- a/cmd/derper/depaware.txt
+++ b/cmd/derper/depaware.txt
@@ -157,6 +157,7 @@ tailscale.com/cmd/derper dependencies: (generated by github.com/tailscale/depawa
         tailscale.com/util/syspolicy                                 from tailscale.com/ipn
         tailscale.com/util/vizerror                                  from tailscale.com/tailcfg+
    W 💣 tailscale.com/util/winutil                                   from tailscale.com/hostinfo+
+   W 💣 tailscale.com/util/winutil/winenv                            from tailscale.com/hostinfo
         tailscale.com/version                                        from tailscale.com/derp+
         tailscale.com/version/distro                                 from tailscale.com/envknob+
         tailscale.com/wgengine/filter                                from tailscale.com/types/netmap
diff --git a/cmd/tailscale/depaware.txt b/cmd/tailscale/depaware.txt
index 9870aeb42..dcd4924ef 100644
--- a/cmd/tailscale/depaware.txt
+++ b/cmd/tailscale/depaware.txt
@@ -166,6 +166,7 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
         tailscale.com/util/vizerror                                  from tailscale.com/tailcfg+
      💣 tailscale.com/util/winutil                                   from tailscale.com/clientupdate+
    W 💣 tailscale.com/util/winutil/authenticode                      from tailscale.com/clientupdate
+   W 💣 tailscale.com/util/winutil/winenv                            from tailscale.com/hostinfo
         tailscale.com/version                                        from tailscale.com/client/web+
         tailscale.com/version/distro                                 from tailscale.com/client/web+
         tailscale.com/wgengine/capture                               from tailscale.com/cmd/tailscale/cli
diff --git a/cmd/tailscaled/depaware.txt b/cmd/tailscaled/depaware.txt
index 5fe355855..06ad2f3f7 100644
--- a/cmd/tailscaled/depaware.txt
+++ b/cmd/tailscaled/depaware.txt
@@ -399,6 +399,7 @@ tailscale.com/cmd/tailscaled dependencies: (generated by github.com/tailscale/de
      💣 tailscale.com/util/winutil                                   from tailscale.com/clientupdate+
    W 💣 tailscale.com/util/winutil/authenticode                      from tailscale.com/clientupdate+
    W    tailscale.com/util/winutil/policy                            from tailscale.com/ipn/ipnlocal
+   W 💣 tailscale.com/util/winutil/winenv                            from tailscale.com/hostinfo
         tailscale.com/util/zstdframe                                 from tailscale.com/control/controlclient+
         tailscale.com/version                                        from tailscale.com/client/web+
         tailscale.com/version/distro                                 from tailscale.com/client/web+
diff --git a/hostinfo/hostinfo_windows.go b/hostinfo/hostinfo_windows.go
index d74d1db42..b789efb28 100644
--- a/hostinfo/hostinfo_windows.go
+++ b/hostinfo/hostinfo_windows.go
@@ -13,18 +13,28 @@ import (
 	"golang.org/x/sys/windows/registry"
 	"tailscale.com/types/ptr"
 	"tailscale.com/util/winutil"
+	"tailscale.com/util/winutil/winenv"
 )
 
 func init() {
+	distroName = lazyDistroName.Get
 	osVersion = lazyOSVersion.Get
 	packageType = lazyPackageType.Get
 }
 
 var (
+	lazyDistroName  = &lazyAtomicValue[string]{f: ptr.To(distroNameWindows)}
 	lazyOSVersion   = &lazyAtomicValue[string]{f: ptr.To(osVersionWindows)}
 	lazyPackageType = &lazyAtomicValue[string]{f: ptr.To(packageTypeWindows)}
 )
 
+func distroNameWindows() string {
+	if winenv.IsWindowsServer() {
+		return "Server"
+	}
+	return ""
+}
+
 func osVersionWindows() string {
 	major, minor, build := windows.RtlGetNtVersionNumbers()
 	s := fmt.Sprintf("%d.%d.%d", major, minor, build)