diff --git a/pkg/cli/bool_flag.go b/pkg/cli/bool_flag.go
index 0730c6bf2b..1b3ffc69b3 100644
--- a/pkg/cli/bool_flag.go
+++ b/pkg/cli/bool_flag.go
@@ -3,6 +3,7 @@ package cli
 import (
 	libflag "flag"
 
+	"github.com/gruntwork-io/go-commons/errors"
 	"github.com/urfave/cli/v2"
 )
 
@@ -42,11 +43,22 @@ func (flag *BoolFlag) Apply(set *libflag.FlagSet) error {
 		flag.Destination = new(bool)
 	}
 
-	var err error
+	var (
+		err      error
+		envValue *string
+	)
 
 	valType := FlagType[bool](&boolFlagType{negative: flag.Negative})
 
-	if flag.FlagValue, err = newGenericValue(valType, flag.LookupEnv(flag.EnvVar), flag.Destination); err != nil {
+	if val := flag.LookupEnv(flag.EnvVar); val != nil && *val != "" {
+		envValue = val
+	}
+
+	if flag.FlagValue, err = newGenericValue(valType, envValue, flag.Destination); err != nil {
+		if envValue != nil {
+			return errors.Errorf("invalid boolean value %q for %s: %w", *envValue, flag.EnvVar, err)
+		}
+
 		return err
 	}
 
diff --git a/pkg/cli/bool_flag_test.go b/pkg/cli/bool_flag_test.go
index 9de3ed49dd..582682f263 100644
--- a/pkg/cli/bool_flag_test.go
+++ b/pkg/cli/bool_flag_test.go
@@ -11,6 +11,7 @@ import (
 	"github.com/gruntwork-io/terragrunt/pkg/cli"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
+	"golang.org/x/exp/maps"
 )
 
 func TestBoolFlagApply(t *testing.T) {
@@ -86,6 +87,20 @@ func TestBoolFlagApply(t *testing.T) {
 			false,
 			errors.New(`invalid boolean flag foo: setting the flag multiple times`),
 		},
+		{
+			cli.BoolFlag{Name: "foo", EnvVar: "FOO"},
+			nil,
+			map[string]string{"FOO": ""},
+			false,
+			nil,
+		},
+		{
+			cli.BoolFlag{Name: "foo", EnvVar: "FOO"},
+			nil,
+			map[string]string{"FOO": "monkey"},
+			false,
+			errors.New(`invalid boolean value "monkey" for FOO: must be one of: "0", "1", "f", "t", "false", "true"`),
+		},
 	}
 
 	for i, testCase := range testCases {
@@ -130,11 +145,12 @@ func testBoolFlagApply(t *testing.T, flag *cli.BoolFlag, args []string, envs map
 	flagSet.SetOutput(io.Discard)
 
 	err := flag.Apply(flagSet)
-	require.NoError(t, err)
+	if err == nil {
+		err = flagSet.Parse(args)
+	}
 
-	err = flagSet.Parse(args)
 	if expectedErr != nil {
-		require.Equal(t, expectedErr, err)
+		require.ErrorContains(t, expectedErr, err.Error())
 		return
 	}
 	require.NoError(t, err)
@@ -148,6 +164,8 @@ func testBoolFlagApply(t *testing.T, flag *cli.BoolFlag, args []string, envs map
 		assert.Equal(t, strconv.FormatBool(expectedValue), flag.GetValue(), "GetValue()")
 	}
 
+	maps.DeleteFunc(envs, func(k, v string) bool { return v == "" })
+
 	assert.Equal(t, len(args) > 0 || len(envs) > 0, flag.Value().IsSet(), "IsSet()")
 	assert.Equal(t, expectedDefaultValue, flag.Value().GetDefaultText(), "GetDefaultText()")
 
diff --git a/pkg/cli/errors.go b/pkg/cli/errors.go
index 1a922a9294..aad91324aa 100644
--- a/pkg/cli/errors.go
+++ b/pkg/cli/errors.go
@@ -88,3 +88,17 @@ func handleExitCoder(err error, osExiter func(code int)) error {
 
 	return err
 }
+
+// InvalidValueError is used to wrap errors from `strconv` to make the error message more user friendly.
+type InvalidValueError struct {
+	underlyingError error
+	msg             string
+}
+
+func (err InvalidValueError) Error() string {
+	return err.msg
+}
+
+func (err InvalidValueError) Unwrap() error {
+	return err.underlyingError
+}
diff --git a/pkg/cli/generic_flag.go b/pkg/cli/generic_flag.go
index b86dd0cb87..6628c9c826 100644
--- a/pkg/cli/generic_flag.go
+++ b/pkg/cli/generic_flag.go
@@ -47,11 +47,22 @@ func (flag *GenericFlag[T]) Apply(set *libflag.FlagSet) error {
 		flag.Destination = new(T)
 	}
 
-	var err error
+	var (
+		err      error
+		envValue *string
+	)
 
 	valType := FlagType[T](new(genericType[T]))
 
-	if flag.FlagValue, err = newGenericValue(valType, flag.LookupEnv(flag.EnvVar), flag.Destination); err != nil {
+	if val := flag.LookupEnv(flag.EnvVar); val != nil {
+		envValue = val
+	}
+
+	if flag.FlagValue, err = newGenericValue(valType, envValue, flag.Destination); err != nil {
+		if envValue != nil {
+			return errors.Errorf("invalid value %q for %s: %w", *envValue, flag.EnvVar, err)
+		}
+
 		return err
 	}
 
@@ -199,7 +210,7 @@ func (val *genericType[T]) Set(str string) error {
 	case *bool:
 		v, err := strconv.ParseBool(str)
 		if err != nil {
-			return errors.Errorf("error parse: %w", err)
+			return errors.WithStackTrace(InvalidValueError{underlyingError: err, msg: `must be one of: "0", "1", "f", "t", "false", "true"`})
 		}
 
 		*dest = v
@@ -207,7 +218,7 @@ func (val *genericType[T]) Set(str string) error {
 	case *int:
 		v, err := strconv.ParseInt(str, 0, strconv.IntSize)
 		if err != nil {
-			return errors.Errorf("error parse: %w", err)
+			return errors.WithStackTrace(InvalidValueError{underlyingError: err, msg: "must be 32-bit integer"})
 		}
 
 		*dest = int(v)
@@ -215,7 +226,7 @@ func (val *genericType[T]) Set(str string) error {
 	case *uint:
 		v, err := strconv.ParseUint(str, 10, 64)
 		if err != nil {
-			return errors.Errorf("error parse: %w", err)
+			return errors.WithStackTrace(InvalidValueError{underlyingError: err, msg: "must be 32-bit unsigned integer"})
 		}
 
 		*dest = uint(v)
@@ -223,7 +234,7 @@ func (val *genericType[T]) Set(str string) error {
 	case *int64:
 		v, err := strconv.ParseInt(str, 0, 64)
 		if err != nil {
-			return errors.Errorf("error parse: %w", err)
+			return errors.WithStackTrace(InvalidValueError{underlyingError: err, msg: "must be 64-bit integer"})
 		}
 
 		*dest = v
diff --git a/pkg/cli/generic_flag_test.go b/pkg/cli/generic_flag_test.go
index 2138274be1..ac864e72ea 100644
--- a/pkg/cli/generic_flag_test.go
+++ b/pkg/cli/generic_flag_test.go
@@ -101,6 +101,13 @@ func TestGenericFlagIntApply(t *testing.T) {
 			20,
 			nil,
 		},
+		{
+			cli.GenericFlag[int]{Name: "foo", EnvVar: "FOO"},
+			[]string{},
+			map[string]string{"FOO": "monkey"},
+			0,
+			errors.New(`invalid value "monkey" for FOO: must be 32-bit integer`),
+		},
 		{
 			cli.GenericFlag[int]{Name: "foo", Destination: mockDestValue(55)},
 			nil,
@@ -145,6 +152,13 @@ func TestGenericFlagInt64Apply(t *testing.T) {
 			20,
 			nil,
 		},
+		{
+			cli.GenericFlag[int64]{Name: "foo", EnvVar: "FOO"},
+			[]string{},
+			map[string]string{"FOO": "monkey"},
+			0,
+			errors.New(`invalid value "monkey" for FOO: must be 64-bit integer`),
+		},
 		{
 			cli.GenericFlag[int64]{Name: "foo", Destination: mockDestValue(int64(55))},
 			nil,
@@ -196,11 +210,12 @@ func testGenericFlagApply[T cli.GenericType](t *testing.T, flag *cli.GenericFlag
 	flagSet.SetOutput(io.Discard)
 
 	err := flag.Apply(flagSet)
-	require.NoError(t, err)
+	if err == nil {
+		err = flagSet.Parse(args)
+	}
 
-	err = flagSet.Parse(args)
 	if expectedErr != nil {
-		require.Equal(t, expectedErr, err)
+		require.ErrorContains(t, expectedErr, err.Error())
 		return
 	}
 	require.NoError(t, err)
diff --git a/pkg/cli/map_flag.go b/pkg/cli/map_flag.go
index 4a7ac691e1..dd28504921 100644
--- a/pkg/cli/map_flag.go
+++ b/pkg/cli/map_flag.go
@@ -76,12 +76,23 @@ func (flag *MapFlag[K, V]) Apply(set *libflag.FlagSet) error {
 		flag.KeyValSep = MapFlagKeyValSep
 	}
 
-	var err error
+	var (
+		err      error
+		envValue *string
+	)
 
 	keyType := FlagType[K](new(genericType[K]))
 	valType := FlagType[V](new(genericType[V]))
 
-	if flag.FlagValue, err = newMapValue(keyType, valType, flag.LookupEnv(flag.EnvVar), flag.EnvVarSep, flag.KeyValSep, flag.Splitter, flag.Destination); err != nil {
+	if val := flag.LookupEnv(flag.EnvVar); val != nil {
+		envValue = val
+	}
+
+	if flag.FlagValue, err = newMapValue(keyType, valType, envValue, flag.EnvVarSep, flag.KeyValSep, flag.Splitter, flag.Destination); err != nil {
+		if envValue != nil {
+			return errors.Errorf("invalid value %q for %s: %w", *envValue, flag.EnvVar, err)
+		}
+
 		return err
 	}
 
diff --git a/pkg/cli/slice_flag.go b/pkg/cli/slice_flag.go
index 3c355fe069..5f25ea1ec6 100644
--- a/pkg/cli/slice_flag.go
+++ b/pkg/cli/slice_flag.go
@@ -4,6 +4,7 @@ import (
 	libflag "flag"
 	"strings"
 
+	"github.com/gruntwork-io/go-commons/errors"
 	"github.com/urfave/cli/v2"
 )
 
@@ -62,11 +63,22 @@ func (flag *SliceFlag[T]) Apply(set *libflag.FlagSet) error {
 		flag.EnvVarSep = SliceFlagEnvVarSep
 	}
 
-	var err error
+	var (
+		err      error
+		envValue *string
+	)
 
 	valType := FlagType[T](new(genericType[T]))
 
-	if flag.FlagValue, err = newSliceValue(valType, flag.LookupEnv(flag.EnvVar), flag.EnvVarSep, flag.Splitter, flag.Destination); err != nil {
+	if val := flag.LookupEnv(flag.EnvVar); val != nil {
+		envValue = val
+	}
+
+	if flag.FlagValue, err = newSliceValue(valType, envValue, flag.EnvVarSep, flag.Splitter, flag.Destination); err != nil {
+		if envValue != nil {
+			return errors.Errorf("invalid value %q for %s: %w", *envValue, flag.EnvVar, err)
+		}
+
 		return err
 	}