diff --git a/cmd/tailscale/cli/diag.go b/cmd/tailscale/cli/diag.go
new file mode 100644
index 000000000..253c8e875
--- /dev/null
+++ b/cmd/tailscale/cli/diag.go
@@ -0,0 +1,55 @@
+// Copyright (c) 2021 Tailscale Inc & AUTHORS All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+// +build linux windows darwin
+
+package cli
+
+import (
+	"fmt"
+	"path/filepath"
+	"runtime"
+	"strings"
+
+	ps "github.com/mitchellh/go-ps"
+)
+
+// fixTailscaledConnectError is called when the local tailscaled has
+// been determined unreachable due to the provided origErr value. It
+// returns either the same error or a better one to help the user
+// understand why tailscaled isn't running for their platform.
+func fixTailscaledConnectError(origErr error) error {
+	procs, err := ps.Processes()
+	if err != nil {
+		return fmt.Errorf("failed to connect to local Tailscaled process and failed to enumerate processes while looking for it")
+	}
+	found := false
+	for _, proc := range procs {
+		base := filepath.Base(proc.Executable())
+		if base == "tailscaled" {
+			found = true
+			break
+		}
+		if runtime.GOOS == "darwin" && base == "IPNExtension" {
+			found = true
+			break
+		}
+		if runtime.GOOS == "windows" && strings.EqualFold(base, "tailscaled.exe") {
+			found = true
+			break
+		}
+	}
+	if !found {
+		switch runtime.GOOS {
+		case "windows":
+			return fmt.Errorf("failed to connect to local tailscaled process; is the Tailscale service running?")
+		case "darwin":
+			return fmt.Errorf("failed to connect to local Tailscale service; is Tailscale running?")
+		case "linux":
+			return fmt.Errorf("failed to connect to local tailscaled; it doesn't appear to be running (sudo systemctl start tailscaled ?)")
+		}
+		return fmt.Errorf("failed to connect to local tailscaled process; it doesn't appear to be running")
+	}
+	return fmt.Errorf("failed to connect to local tailscaled (which appears to be running). Got error: %w", origErr)
+}
diff --git a/cmd/tailscale/cli/diag_other.go b/cmd/tailscale/cli/diag_other.go
new file mode 100644
index 000000000..bc67cbeee
--- /dev/null
+++ b/cmd/tailscale/cli/diag_other.go
@@ -0,0 +1,16 @@
+// Copyright (c) 2021 Tailscale Inc & AUTHORS All rights reserved.
+// Use of this source code is governed by a BSD-style
+// license that can be found in the LICENSE file.
+
+// +build !linux,!windows,!darwin
+
+package cli
+
+import "fmt"
+
+// The github.com/mitchellh/go-ps package doesn't work on all platforms,
+// so just don't diagnose connect failures.
+
+func fixTailscaledConnectError(origErr error) error {
+	return fmt.Errorf("failed to connect to local tailscaled process (is it running?); got: %w", origErr)
+}
diff --git a/cmd/tailscale/cli/status.go b/cmd/tailscale/cli/status.go
index af887f427..9ae378350 100644
--- a/cmd/tailscale/cli/status.go
+++ b/cmd/tailscale/cli/status.go
@@ -57,7 +57,7 @@ var statusArgs struct {
 func runStatus(ctx context.Context, args []string) error {
 	st, err := tailscale.Status(ctx)
 	if err != nil {
-		return err
+		return fixTailscaledConnectError(err)
 	}
 	if statusArgs.json {
 		if statusArgs.active {
diff --git a/cmd/tailscale/cli/up.go b/cmd/tailscale/cli/up.go
index 8c39bbd44..c6f5909cd 100644
--- a/cmd/tailscale/cli/up.go
+++ b/cmd/tailscale/cli/up.go
@@ -294,7 +294,7 @@ func runUp(ctx context.Context, args []string) error {
 
 	st, err := tailscale.Status(ctx)
 	if err != nil {
-		fatalf("can't fetch status from tailscaled: %v", err)
+		return fixTailscaledConnectError(err)
 	}
 	origAuthURL := st.AuthURL
 
diff --git a/cmd/tailscale/depaware.txt b/cmd/tailscale/depaware.txt
index 26a459de7..dfc160e37 100644
--- a/cmd/tailscale/depaware.txt
+++ b/cmd/tailscale/depaware.txt
@@ -4,6 +4,7 @@ tailscale.com/cmd/tailscale dependencies: (generated by github.com/tailscale/dep
    W    github.com/alexbrainman/sspi/internal/common                 from github.com/alexbrainman/sspi/negotiate
    W 💣 github.com/alexbrainman/sspi/negotiate                       from tailscale.com/net/tshttpproxy
         github.com/kballard/go-shellquote                            from tailscale.com/cmd/tailscale/cli
+     💣 github.com/mitchellh/go-ps                                   from tailscale.com/cmd/tailscale/cli
         github.com/peterbourgon/ff/v2                                from github.com/peterbourgon/ff/v2/ffcli
         github.com/peterbourgon/ff/v2/ffcli                          from tailscale.com/cmd/tailscale/cli
         github.com/tcnksm/go-httpstat                                from tailscale.com/net/netcheck
diff --git a/go.mod b/go.mod
index 73725326d..6fa065348 100644
--- a/go.mod
+++ b/go.mod
@@ -23,6 +23,7 @@ require (
 	github.com/mdlayher/netlink v1.4.1
 	github.com/mdlayher/sdnotify v0.0.0-20210228150836-ea3ec207d697
 	github.com/miekg/dns v1.1.42
+	github.com/mitchellh/go-ps v1.0.0
 	github.com/pborman/getopt v1.1.0
 	github.com/peterbourgon/ff/v2 v2.0.0
 	github.com/pkg/sftp v1.13.0
diff --git a/go.sum b/go.sum
index 61e3e9d89..e86c8ca28 100644
--- a/go.sum
+++ b/go.sum
@@ -418,6 +418,7 @@ github.com/mitchellh/copystructure v1.0.0/go.mod h1:SNtv71yrdKgLRyLFxmLdkAbkKEFW
 github.com/mitchellh/go-homedir v1.0.0/go.mod h1:SfyaCUpYCn1Vlf4IUYiD9fPX4A5wJrkLzIz1N1q0pr0=
 github.com/mitchellh/go-homedir v1.1.0 h1:lukF9ziXFxDFPkA1vsr5zpc1XuPDn/wFntq5mG+4E0Y=
 github.com/mitchellh/go-homedir v1.1.0/go.mod h1:SfyaCUpYCn1Vlf4IUYiD9fPX4A5wJrkLzIz1N1q0pr0=
+github.com/mitchellh/go-ps v1.0.0 h1:i6ampVEEF4wQFF+bkYfwYgY+F/uYJDktmvLPf7qIgjc=
 github.com/mitchellh/go-ps v1.0.0/go.mod h1:J4lOc8z8yJs6vUwklHw2XEIiT4z4C40KtWVN3nvg8Pg=
 github.com/mitchellh/go-testing-interface v1.0.0/go.mod h1:kRemZodwjscx+RGhAo8eIhFbs2+BFgRtFPeD/KE+zxI=
 github.com/mitchellh/gox v0.4.0/go.mod h1:Sd9lOJ0+aimLBi73mGofS1ycjY8lL3uZM3JPS42BGNg=