diff --git a/go.mod b/go.mod
index eba1883eca55a..51571bc34c3bb 100644
--- a/go.mod
+++ b/go.mod
@@ -40,7 +40,7 @@ replace github.com/tcnksm/go-httpstat => github.com/kylecarbs/go-httpstat v0.0.0
 
 // There are a few minor changes we make to Tailscale that we're slowly upstreaming. Compare here:
 // https://github.com/tailscale/tailscale/compare/main...coder:tailscale:main
-replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20230321171725-fed359a0cafa
+replace tailscale.com => github.com/coder/tailscale v1.1.1-0.20230323204624-bf5761af4a29
 
 // Switch to our fork that imports fixes from http://github.com/tailscale/ssh.
 // See: https://github.com/coder/coder/issues/3371
@@ -60,7 +60,6 @@ require (
 	github.com/AlecAivazis/survey/v2 v2.3.5
 	github.com/acarl005/stripansi v0.0.0-20180116102854-5a71ef0e047d
 	github.com/adrg/xdg v0.4.0
-	github.com/ammario/prefixsuffix v0.0.0-20200405191514-5a0456bf2cfd
 	github.com/andybalholm/brotli v1.0.4
 	github.com/armon/circbuf v0.0.0-20190214190532-5111143e8da2
 	github.com/awalterschulze/gographviz v2.0.3+incompatible
@@ -162,7 +161,6 @@ require (
 	golang.org/x/sync v0.1.0
 	golang.org/x/sys v0.5.0
 	golang.org/x/term v0.5.0
-	golang.org/x/text v0.7.0
 	golang.org/x/tools v0.6.0
 	golang.org/x/xerrors v0.0.0-20220907171357-04be3eba64a2
 	golang.zx2c4.com/wireguard v0.0.0-20230223181233-21636207a675
@@ -193,6 +191,7 @@ require (
 	github.com/modern-go/concurrent v0.0.0-20180306012644-bacd9c7ef1dd // indirect
 	github.com/modern-go/reflect2 v1.0.2 // indirect
 	github.com/muesli/cancelreader v0.2.2 // indirect
+	golang.org/x/text v0.7.0 // indirect
 	golang.zx2c4.com/wireguard/wgctrl v0.0.0-20230215201556-9c5414ab4bde // indirect
 )
 
diff --git a/go.sum b/go.sum
index 58d3cd6a3db8b..66b554e3bb4f0 100644
--- a/go.sum
+++ b/go.sum
@@ -193,8 +193,6 @@ github.com/alexbrainman/sspi v0.0.0-20210105120005-909beea2cc74/go.mod h1:cEWa1L
 github.com/alexflint/go-filemutex v0.0.0-20171022225611-72bdc8eae2ae/go.mod h1:CgnQgUtFrFz9mxFNtED3jI5tLDjKlOM+oUF/sTk6ps0=
 github.com/alexflint/go-filemutex v1.1.0/go.mod h1:7P4iRhttt/nUvUOrYIhcpMzv2G6CY9UnI16Z+UJqRyk=
 github.com/alexkohler/prealloc v1.0.0/go.mod h1:VetnK3dIgFBBKmg0YnD9F9x6Icjd+9cvfHR56wJVlKE=
-github.com/ammario/prefixsuffix v0.0.0-20200405191514-5a0456bf2cfd h1:WOzjyD34+0vVw3wzE7js8Yvzo08ljzvK1jG6wL8elVU=
-github.com/ammario/prefixsuffix v0.0.0-20200405191514-5a0456bf2cfd/go.mod h1:VM1c/0Tl3O26UkHMbU32VFqLwLvi2FA40b6s5vPOpoo=
 github.com/andreyvit/diff v0.0.0-20170406064948-c7f18ee00883 h1:bvNMNQO63//z+xNgfBlViaCIJKLlCJ6/fmUseuG0wVQ=
 github.com/andybalholm/brotli v1.0.2/go.mod h1:loMXtMfwqflxFJPmdbJO0a3KNoPuLBgiu3qAvBg8x/Y=
 github.com/andybalholm/brotli v1.0.3/go.mod h1:fO7iG3H7G2nSZ7m0zPUDn85XEX2GTukHGRSepvi9Eig=
@@ -380,8 +378,8 @@ github.com/coder/retry v1.3.1-0.20230210155434-e90a2e1e091d h1:09JG37IgTB6n3ouX9
 github.com/coder/retry v1.3.1-0.20230210155434-e90a2e1e091d/go.mod h1:r+1J5i/989wt6CUeNSuvFKKA9hHuKKPMxdzDbTuvwwk=
 github.com/coder/ssh v0.0.0-20220811105153-fcea99919338 h1:tN5GKFT68YLVzJoA8AHuiMNJ0qlhoD3pGN3JY9gxSko=
 github.com/coder/ssh v0.0.0-20220811105153-fcea99919338/go.mod h1:ZSS+CUoKHDrqVakTfTWUlKSr9MtMFkC4UvtQKD7O914=
-github.com/coder/tailscale v1.1.1-0.20230321171725-fed359a0cafa h1:EjRGgTz7BUECmbV8jHTi1/rKdDjJESGSlm1Jp7evvCQ=
-github.com/coder/tailscale v1.1.1-0.20230321171725-fed359a0cafa/go.mod h1:jpg+77g19FpXL43U1VoIqoSg1K/Vh5CVxycGldQ8KhA=
+github.com/coder/tailscale v1.1.1-0.20230323204624-bf5761af4a29 h1:bZAOib5uT7ohTYcKKj8w5jH+HwBStBrZ/KcU26X0g+A=
+github.com/coder/tailscale v1.1.1-0.20230323204624-bf5761af4a29/go.mod h1:jpg+77g19FpXL43U1VoIqoSg1K/Vh5CVxycGldQ8KhA=
 github.com/coder/terraform-provider-coder v0.6.21 h1:TIH6+/VQFreT8q/CkRvpHtbIeM5cOAhuDS5Sh1Nm21Q=
 github.com/coder/terraform-provider-coder v0.6.21/go.mod h1:UIfU3bYNeSzJJvHyJ30tEKjD6Z9utloI+HUM/7n94CY=
 github.com/coder/wgtunnel v0.1.5 h1:WP3sCj/3iJ34eKvpMQEp1oJHvm24RYh0NHbj1kfUKfs=
diff --git a/tailnet/conn_test.go b/tailnet/conn_test.go
index fcf714a974a8c..8f00c3c45a8de 100644
--- a/tailnet/conn_test.go
+++ b/tailnet/conn_test.go
@@ -160,7 +160,7 @@ func TestTailnet(t *testing.T) {
 		node := <-nodes
 		require.Len(t, node.DERPForcedWebsocket, 1)
 		// Ensure the reason is valid!
-		require.Equal(t, "GET failed with status code 400: Invalid \"Upgrade\" header: DERP", node.DERPForcedWebsocket[derpMap.RegionIDs()[0]])
+		require.Equal(t, `GET failed with status code 400 (a proxy could be disallowing the use of 'Upgrade: derp'): Invalid "Upgrade" header: DERP`, node.DERPForcedWebsocket[derpMap.RegionIDs()[0]])
 
 		w1.Close()
 		w2.Close()