diff --git a/client.go b/client.go
index 2e86f621..33bc85a5 100644
--- a/client.go
+++ b/client.go
@@ -6,6 +6,9 @@ import (
 	"crypto/subtle"
 	"crypto/tls"
 	"crypto/x509"
+	"debug/elf"
+	"debug/macho"
+	"debug/pe"
 	"encoding/base64"
 	"errors"
 	"fmt"
@@ -15,17 +18,28 @@ import (
 	"net"
 	"os"
 	"os/exec"
+	"os/user"
 	"path/filepath"
+	"runtime"
 	"strconv"
 	"strings"
 	"sync"
 	"sync/atomic"
+	"syscall"
 	"time"
 
 	"github.com/hashicorp/go-hclog"
 	"google.golang.org/grpc"
 )
 
+const unrecognizedRemotePluginMessage = `Unrecognized remote plugin message: %s
+This usually means
+  the plugin was not compiled for this architecture,
+  the plugin is missing dynamic-link libraries necessary to run,
+  the plugin is not executable by this process due to file permissions, or
+  the plugin failed to negotiate the initial go-plugin protocol handshake
+%s`
+
 // If this is 1, then we've called CleanupClients. This can be used
 // by plugin RPC implementations to change error behavior since you
 // can expected network connection errors at this point. This should be
@@ -473,7 +487,65 @@ func (c *Client) Kill() {
 	c.l.Unlock()
 }
 
-// Starts the underlying subprocess, communicating with it to negotiate
+// peTypes is a list of Portable Executable (PE) machine types from https://learn.microsoft.com/en-us/windows/win32/debug/pe-format
+// mapped to GOARCH types. It is not comprehensive, and only includes machine types that Go supports.
+var peTypes = map[uint16]string{
+	0x14c:  "386",
+	0x1c0:  "arm",
+	0x6264: "loong64",
+	0x8664: "amd64",
+	0xaa64: "arm64",
+}
+
+// additionalNotesAboutCommand tries to get additional information about a command that might help diagnose
+// why it won't run correctly. It runs as a best effort only.
+func additionalNotesAboutCommand(path string) string {
+	notes := ""
+	stat, err := os.Stat(path)
+	if err != nil {
+		return notes
+	}
+
+	notes += "\nAdditional notes about plugin:\n"
+	notes += fmt.Sprintf("  Path: %s\n", path)
+	notes += fmt.Sprintf("  Mode: %s\n", stat.Mode())
+	statT, ok := stat.Sys().(*syscall.Stat_t)
+	if ok {
+		currentUsername := "?"
+		if u, err := user.LookupId(strconv.FormatUint(uint64(os.Getuid()), 10)); err == nil {
+			currentUsername = u.Username
+		}
+		currentGroup := "?"
+		if g, err := user.LookupGroupId(strconv.FormatUint(uint64(os.Getgid()), 10)); err == nil {
+			currentGroup = g.Name
+		}
+		username := "?"
+		if u, err := user.LookupId(strconv.FormatUint(uint64(statT.Uid), 10)); err == nil {
+			username = u.Username
+		}
+		group := "?"
+		if g, err := user.LookupGroupId(strconv.FormatUint(uint64(statT.Gid), 10)); err == nil {
+			group = g.Name
+		}
+		notes += fmt.Sprintf("  Owner: %d [%s] (current: %d [%s])\n", statT.Uid, username, os.Getuid(), currentUsername)
+		notes += fmt.Sprintf("  Group: %d [%s] (current: %d [%s])\n", statT.Gid, group, os.Getgid(), currentGroup)
+	}
+
+	if elfFile, err := elf.Open(path); err == nil {
+		notes += fmt.Sprintf("  ELF architecture: %s (current architecture: %s)\n", elfFile.Machine, runtime.GOARCH)
+	} else if machoFile, err := macho.Open(path); err == nil {
+		notes += fmt.Sprintf("  MachO architecture: %s (current architecture: %s)\n", machoFile.Cpu, runtime.GOARCH)
+	} else if peFile, err := pe.Open(path); err == nil {
+		machine, ok := peTypes[peFile.Machine]
+		if !ok {
+			machine = "unknown"
+		}
+		notes += fmt.Sprintf("  PE architecture: %s (current architecture: %s)\n", machine, runtime.GOARCH)
+	}
+	return notes
+}
+
+// Start the underlying subprocess, communicating with it to negotiate
 // a port for RPC connections, and returning the address to connect via RPC.
 //
 // This method is safe to call multiple times. Subsequent calls have no effect.
@@ -697,10 +769,7 @@ func (c *Client) Start() (addr net.Addr, err error) {
 		line = strings.TrimSpace(line)
 		parts := strings.SplitN(line, "|", 6)
 		if len(parts) < 4 {
-			err = fmt.Errorf(
-				"Unrecognized remote plugin message: %s\n\n"+
-					"This usually means that the plugin is either invalid or simply\n"+
-					"needs to be recompiled to support the latest protocol.", line)
+			err = fmt.Errorf(unrecognizedRemotePluginMessage, line, additionalNotesAboutCommand(cmd.Path))
 			return
 		}
 
diff --git a/client_test.go b/client_test.go
index 7c821545..176234f2 100644
--- a/client_test.go
+++ b/client_test.go
@@ -10,13 +10,14 @@ import (
 	"net"
 	"os"
 	"os/exec"
+	"path"
 	"path/filepath"
 	"strings"
 	"sync"
 	"testing"
 	"time"
 
-	hclog "github.com/hashicorp/go-hclog"
+	"github.com/hashicorp/go-hclog"
 )
 
 func TestClient(t *testing.T) {
@@ -1395,3 +1396,42 @@ this line is short
 		t.Fatalf("\nexpected output: %q\ngot output:      %q", msg, read)
 	}
 }
+
+func TestAdditionalNotesAboutCommand(t *testing.T) {
+	files := []string{
+		"windows-amd64.exe",
+		"windows-386.exe",
+		"linux-amd64",
+		"darwin-amd64",
+		"darwin-arm64",
+	}
+	for _, file := range files {
+		fullFile := path.Join("testdata", file)
+		if _, err := os.Stat(fullFile); os.IsNotExist(err) {
+			t.Skipf("testdata executables not present; please run 'make' in testdata/ directory for this test")
+		}
+
+		notes := additionalNotesAboutCommand(fullFile)
+		if strings.Contains(file, "windows") && !strings.Contains(notes, "PE") {
+			t.Errorf("Expected notes to contain Windows information:\n%s", notes)
+		}
+		if strings.Contains(file, "linux") && !strings.Contains(notes, "ELF") {
+			t.Errorf("Expected notes to contain Linux information:\n%s", notes)
+		}
+		if strings.Contains(file, "darwin") && !strings.Contains(notes, "MachO") {
+			t.Errorf("Expected notes to contain macOS information:\n%s", notes)
+		}
+
+		if strings.Contains(file, "amd64") && !(strings.Contains(notes, "amd64") || strings.Contains(notes, "EM_X86_64") || strings.Contains(notes, "CpuAmd64")) {
+			t.Errorf("Expected notes to contain amd64 information:\n%s", notes)
+		}
+
+		if strings.Contains(file, "arm64") && !strings.Contains(notes, "CpuArm64") {
+			t.Errorf("Expected notes to contain arm64 information:\n%s", notes)
+		}
+		if strings.Contains(file, "386") && !strings.Contains(notes, "386") {
+			t.Errorf("Expected notes to contain 386 information:\n%s", notes)
+		}
+
+	}
+}
diff --git a/plugin_test.go b/plugin_test.go
index 7ce24aa6..ba5e9839 100644
--- a/plugin_test.go
+++ b/plugin_test.go
@@ -15,7 +15,7 @@ import (
 	"time"
 
 	"github.com/golang/protobuf/ptypes/empty"
-	hclog "github.com/hashicorp/go-hclog"
+	"github.com/hashicorp/go-hclog"
 	grpctest "github.com/hashicorp/go-plugin/test/grpc"
 	"golang.org/x/net/context"
 	"google.golang.org/grpc"
diff --git a/testdata/.gitignore b/testdata/.gitignore
new file mode 100644
index 00000000..81665891
--- /dev/null
+++ b/testdata/.gitignore
@@ -0,0 +1,5 @@
+windows-amd64.exe
+windows-386.exe
+linux-amd64
+darwin-amd64
+darwin-arm64
diff --git a/testdata/Makefile b/testdata/Makefile
new file mode 100644
index 00000000..85ce1be6
--- /dev/null
+++ b/testdata/Makefile
@@ -0,0 +1,29 @@
+default: all
+.PHONY: default
+
+.PHONY: clean
+clean:
+	rm -f windows-amd64.exe windows-386.exe linux-amd64 darwin-amd64 darwin-arm64
+
+.PHONY: all
+all: windows-amd64.exe windows-386.exe linux-amd64 darwin-amd64 darwin-arm64
+
+.PHONY: windows-amd64.exe
+windows-amd64.exe:
+	GOOS=windows GOARCH=amd64 go build -o $@
+
+.PHONY: windows-386.exe
+windows-386.exe:
+	GOOS=windows GOARCH=386 go build -o $@
+
+.PHONY: linux-amd64
+linux-amd64:
+	GOOS=linux GOARCH=amd64 go build -o $@
+
+.PHONY: darwin-amd64
+darwin-amd64:
+	GOOS=darwin GOARCH=amd64 go build -o $@
+
+.PHONY: darwin-arm64
+darwin-arm64:
+	GOOS=darwin GOARCH=arm64 go build -o $@
\ No newline at end of file
diff --git a/testdata/README.md b/testdata/README.md
new file mode 100644
index 00000000..cb81911d
--- /dev/null
+++ b/testdata/README.md
@@ -0,0 +1 @@
+This folder contains a minimal Go program so that we can obtain example binaries of programs for various architectures for use in tests.
\ No newline at end of file
diff --git a/testdata/go.mod b/testdata/go.mod
new file mode 100644
index 00000000..68834454
--- /dev/null
+++ b/testdata/go.mod
@@ -0,0 +1,3 @@
+module example.com/testdata
+
+go 1.19
diff --git a/testdata/go.sum b/testdata/go.sum
new file mode 100644
index 00000000..e69de29b
diff --git a/testdata/minimal.go b/testdata/minimal.go
new file mode 100644
index 00000000..da29a2ca
--- /dev/null
+++ b/testdata/minimal.go
@@ -0,0 +1,4 @@
+package main
+
+func main() {
+}