diff --git a/cmd/cmdtest.go b/cmd/cmdtest.go
index a3999f9b..20fea899 100644
--- a/cmd/cmdtest.go
+++ b/cmd/cmdtest.go
@@ -2,6 +2,7 @@ package cmd
 
 import (
 	"bytes"
+	"fmt"
 	"io"
 	"os"
 	"testing"
@@ -69,3 +70,10 @@ func SetupTestEnvVars(_ *testing.T) func(t *testing.T) {
 		os.Unsetenv("LD_BASE_URI")
 	}
 }
+
+func ExtraErrorHelp(cmdName string, cmdAction string) string {
+	out := ".\n\nUse `ldcli config --set access-token <value>` to configure the value to persist across CLI commands."
+	out += fmt.Sprintf("\n\nSee `ldcli %s %s --help` for supported flags and usage.", cmdName, cmdAction)
+
+	return out
+}
diff --git a/cmd/environments/get_test.go b/cmd/environments/get_test.go
index 9dba82ac..b7645465 100644
--- a/cmd/environments/get_test.go
+++ b/cmd/environments/get_test.go
@@ -99,7 +99,7 @@ func TestGet(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "environment", "project" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "environment", "project" not set`+cmd.ExtraErrorHelp("environments", "get"))
 	})
 
 	t.Run("with missing short flag value is an error", func(t *testing.T) {
diff --git a/cmd/flags/create_test.go b/cmd/flags/create_test.go
index adc98ed8..6ad10c87 100644
--- a/cmd/flags/create_test.go
+++ b/cmd/flags/create_test.go
@@ -99,7 +99,7 @@ func TestCreate(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "data", "project" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "data", "project" not set`+cmd.ExtraErrorHelp("flags", "create"))
 	})
 
 	t.Run("with missing short flag value is an error", func(t *testing.T) {
diff --git a/cmd/flags/get_test.go b/cmd/flags/get_test.go
index 39320d63..3ccd5bae 100644
--- a/cmd/flags/get_test.go
+++ b/cmd/flags/get_test.go
@@ -101,7 +101,7 @@ func TestGet(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "environment", "flag", "project" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "environment", "flag", "project" not set`+cmd.ExtraErrorHelp("flags", "get"))
 	})
 
 	t.Run("with invalid base-uri is an error", func(t *testing.T) {
diff --git a/cmd/flags/update_test.go b/cmd/flags/update_test.go
index a8e2c999..3b6ef128 100644
--- a/cmd/flags/update_test.go
+++ b/cmd/flags/update_test.go
@@ -108,7 +108,7 @@ func TestUpdate(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "data", "flag", "project" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "data", "flag", "project" not set`+cmd.ExtraErrorHelp("flags", "update"))
 	})
 
 	t.Run("with invalid base-uri is an error", func(t *testing.T) {
@@ -235,7 +235,7 @@ func TestToggle(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "environment", "flag", "project" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "environment", "flag", "project" not set`+cmd.ExtraErrorHelp("flags", "toggle-on"))
 	})
 
 	t.Run("with invalid base-uri is an error", func(t *testing.T) {
diff --git a/cmd/members/create_test.go b/cmd/members/create_test.go
index ad102cc5..21cdd174 100644
--- a/cmd/members/create_test.go
+++ b/cmd/members/create_test.go
@@ -105,7 +105,7 @@ func TestCreate(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "data" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "data" not set`+cmd.ExtraErrorHelp("members", "create"))
 	})
 
 	t.Run("with invalid base-uri is an error", func(t *testing.T) {
@@ -131,7 +131,7 @@ func TestCreate(t *testing.T) {
 				"access-token",
 				"base-uri",
 				"data",
-        "output",
+				"output",
 			}, analytics.SUCCESS)
 
 		client := members.MockClient{}
diff --git a/cmd/members/invite_test.go b/cmd/members/invite_test.go
index 4e8e2d85..9ee704d8 100644
--- a/cmd/members/invite_test.go
+++ b/cmd/members/invite_test.go
@@ -105,7 +105,7 @@ func TestInvite(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "emails" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "emails" not set`+cmd.ExtraErrorHelp("members", "invite"))
 	})
 
 	t.Run("with invalid base-uri is an error", func(t *testing.T) {
@@ -131,7 +131,7 @@ func TestInvite(t *testing.T) {
 				"access-token",
 				"base-uri",
 				"emails",
-        "output",
+				"output",
 			}, analytics.SUCCESS)
 
 		client := members.MockClient{}
diff --git a/cmd/projects/create_test.go b/cmd/projects/create_test.go
index 0b9e62f1..ba22ac5a 100644
--- a/cmd/projects/create_test.go
+++ b/cmd/projects/create_test.go
@@ -104,7 +104,7 @@ func TestCreate(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token", "data" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token", "data" not set`+cmd.ExtraErrorHelp("projects", "create"))
 	})
 
 	t.Run("with missing short flag value is an error", func(t *testing.T) {
diff --git a/cmd/projects/list_test.go b/cmd/projects/list_test.go
index 70ed2a0a..64236aa4 100644
--- a/cmd/projects/list_test.go
+++ b/cmd/projects/list_test.go
@@ -99,7 +99,7 @@ func TestList(t *testing.T) {
 
 		_, err := cmd.CallCmd(t, clients, &analytics.NoopClient{}, args)
 
-		assert.EqualError(t, err, `required flag(s) "access-token" not set`+errorHelp)
+		assert.EqualError(t, err, `required flag(s) "access-token" not set`+cmd.ExtraErrorHelp("projects", "list"))
 	})
 
 	t.Run("with missing long flag value is an error", func(t *testing.T) {
diff --git a/cmd/validators/validators.go b/cmd/validators/validators.go
index 8e29e0e8..8aea217c 100644
--- a/cmd/validators/validators.go
+++ b/cmd/validators/validators.go
@@ -4,6 +4,7 @@ import (
 	"errors"
 	"fmt"
 	"net/url"
+	"strings"
 
 	"github.com/spf13/cobra"
 	"github.com/spf13/pflag"
@@ -39,11 +40,16 @@ func Validate() cobra.PositionalArgs {
 }
 
 func CmdError(err error, commandPath string) error {
-	errorMessage := fmt.Sprintf(
-		"%s. See `%s --help` for supported flags and usage.",
-		err.Error(),
-		commandPath,
-	)
+	errorMessage := err.Error() + "."
+
+	// show additional help if a missing flag can be set in the config file
+	if strings.Contains(err.Error(), cliflags.AccessTokenFlag) {
+		errorMessage += "\n\n"
+		errorMessage += fmt.Sprintf("Use `ldcli config --set %s <value>` to configure the value to persist across CLI commands.\n\n", cliflags.AccessTokenFlag)
+	} else {
+		errorMessage += " "
+	}
+	errorMessage += fmt.Sprintf("See `%s --help` for supported flags and usage.", commandPath)
 
 	return errors.New(errorMessage)
 }
diff --git a/cmd/validators/validators_test.go b/cmd/validators/validators_test.go
new file mode 100644
index 00000000..718c76e0
--- /dev/null
+++ b/cmd/validators/validators_test.go
@@ -0,0 +1,37 @@
+package validators_test
+
+import (
+	"errors"
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+
+	"ldcli/cmd/validators"
+)
+
+func TestCmdError(t *testing.T) {
+	t.Run("with missing access-token value shows additional help", func(t *testing.T) {
+		var expected string
+		expected += "required flag(s) \"access-token\" not set.\n\n"
+		expected += "Use `ldcli config --set access-token <value>` to configure the value to persist across CLI commands.\n\n"
+		expected += "See `ldcli command action --help` for supported flags and usage."
+
+		err := validators.CmdError(
+			errors.New(`required flag(s) "access-token" not set`),
+			"ldcli command action",
+		)
+
+		assert.EqualError(t, err, expected)
+	})
+
+	t.Run("with missing other flag value shows regular help", func(t *testing.T) {
+		expected := "required flag(s) \"my-flag\" not set. See `ldcli command action --help` for supported flags and usage."
+
+		err := validators.CmdError(
+			errors.New(`required flag(s) "my-flag" not set`),
+			"ldcli command action",
+		)
+
+		assert.EqualError(t, err, expected)
+	})
+}