diff --git a/pkg/overlay/foldedscalar.go b/pkg/overlay/foldedscalar.go
new file mode 100644
index 000000000..726892195
--- /dev/null
+++ b/pkg/overlay/foldedscalar.go
@@ -0,0 +1,36 @@
+package overlay
+
+import (
+	"strings"
+
+	"gopkg.in/yaml.v3"
+)
+
+// Block indentation is stripped on decode, so leading whitespace means more-indented.
+func hasMoreIndentedLine(value string) bool {
+	for _, line := range strings.Split(value, "\n") {
+		if line == "" {
+			continue
+		}
+		if line[0] == ' ' || line[0] == '\t' {
+			return true
+		}
+	}
+
+	return false
+}
+
+// yaml.v3 injects a line break before more-indented lines in folded scalars on every encode; literal blocks round trip unchanged.
+func stabilizeFoldedScalars(node *yaml.Node) {
+	if node == nil {
+		return
+	}
+
+	if node.Kind == yaml.ScalarNode && node.Style == yaml.FoldedStyle && hasMoreIndentedLine(node.Value) {
+		node.Style = yaml.LiteralStyle
+	}
+
+	for _, child := range node.Content {
+		stabilizeFoldedScalars(child)
+	}
+}
diff --git a/pkg/overlay/foldedscalar_test.go b/pkg/overlay/foldedscalar_test.go
new file mode 100644
index 000000000..938fb0129
--- /dev/null
+++ b/pkg/overlay/foldedscalar_test.go
@@ -0,0 +1,127 @@
+package overlay
+
+import (
+	"testing"
+
+	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
+	"gopkg.in/yaml.v3"
+)
+
+const foldedWithMoreIndentedLine = `description: >-
+  ### Authorization
+
+  | Type | Scopes |
+  | ---- | ------ |
+   | Organization | ` + "`manage_passwords`" + ` |
+`
+
+func roundTrip(t *testing.T, doc string, stabilize bool) string {
+	t.Helper()
+
+	var node yaml.Node
+	require.NoError(t, yaml.Unmarshal([]byte(doc), &node))
+
+	if stabilize {
+		stabilizeFoldedScalars(&node)
+	}
+
+	out, err := yaml.Marshal(&node)
+	require.NoError(t, err)
+
+	return string(out)
+}
+
+func decodeDescription(t *testing.T, doc string) string {
+	t.Helper()
+
+	var decoded struct {
+		Description string `yaml:"description"`
+	}
+	require.NoError(t, yaml.Unmarshal([]byte(doc), &decoded))
+
+	return decoded.Description
+}
+
+func TestStabilizeFoldedScalarsSurvivesRepeatedApplies(t *testing.T) {
+	t.Parallel()
+
+	want := decodeDescription(t, foldedWithMoreIndentedLine)
+
+	doc := foldedWithMoreIndentedLine
+	for i := range 30 {
+		doc = roundTrip(t, doc, true)
+		assert.Equal(t, want, decodeDescription(t, doc), "value changed after %d applies", i+1)
+	}
+}
+
+// Fails once gopkg.in/yaml.v3 fixes the emitter, at which point stabilizeFoldedScalars can go.
+func TestFoldedScalarGrowsWithoutStabilizer(t *testing.T) {
+	t.Parallel()
+
+	before := decodeDescription(t, foldedWithMoreIndentedLine)
+	after := decodeDescription(t, roundTrip(t, foldedWithMoreIndentedLine, false))
+
+	assert.NotEqual(t, before, after)
+}
+
+func TestStabilizeFoldedScalarsLeavesStableStylesAlone(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name string
+		doc  string
+	}{
+		{
+			name: "folded scalar with no more-indented line",
+			doc:  "description: >-\n  one line\n  another line\n",
+		},
+		{
+			name: "literal scalar with more-indented line",
+			doc:  "description: |-\n  one line\n   more indented\n",
+		},
+		{
+			name: "plain scalar",
+			doc:  "description: just a string\n",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			want := decodeDescription(t, tt.doc)
+
+			doc := tt.doc
+			for range 5 {
+				doc = roundTrip(t, doc, true)
+				assert.Equal(t, want, decodeDescription(t, doc))
+			}
+		})
+	}
+}
+
+func TestHasMoreIndentedLine(t *testing.T) {
+	t.Parallel()
+
+	tests := []struct {
+		name  string
+		value string
+		want  bool
+	}{
+		{name: "no indentation", value: "one\ntwo", want: false},
+		{name: "space indented line", value: "one\n two", want: true},
+		{name: "tab indented line", value: "one\n\ttwo", want: true},
+		{name: "blank lines only", value: "one\n\ntwo", want: false},
+		{name: "empty", value: "", want: false},
+		{name: "first line indented", value: " one\ntwo", want: true},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			t.Parallel()
+
+			assert.Equal(t, tt.want, hasMoreIndentedLine(tt.value))
+		})
+	}
+}
diff --git a/pkg/overlay/overlay.go b/pkg/overlay/overlay.go
index 93b791239..159c3232d 100644
--- a/pkg/overlay/overlay.go
+++ b/pkg/overlay/overlay.go
@@ -120,6 +120,8 @@ func apply(document *yaml.Node, o *overlay.Overlay, sourceLocation string, yamlI
 		}
 	}
 
+	stabilizeFoldedScalars(document)
+
 	bytes, err := schemas.RenderDocument(document, sourceLocation, yamlIn, yamlOut)
 	if err != nil {
 		return fmt.Errorf("failed to Render document: %w", err)