diff --git a/README.md b/README.md
index 789f795..88ec91d 100644
--- a/README.md
+++ b/README.md
@@ -78,6 +78,11 @@ render:
     - name: SecretObjectReference
       package: sigs.k8s.io/gateway-api/apis/v1beta1
       link: https://gateway-api.sigs.k8s.io/references/spec/#gateway.networking.k8s.io/v1beta1.SecretObjectReference
+  # Rewrite plain URLs in field and type doc comments to Markdown links. Markdown renderer only.
+  linkMappings:
+    - url: https://example.com/old-page
+      link: docs-content://new/page.md
+      text: New page
 ```
 
 ### Advanced Features
diff --git a/config/config.go b/config/config.go
index b1c792e..9c40f3d 100644
--- a/config/config.go
+++ b/config/config.go
@@ -52,8 +52,9 @@ const (
 )
 
 type RenderConfig struct {
-	KnownTypes        []*KnownType `json:"knownTypes"`
-	KubernetesVersion string       `json:"kubernetesVersion"`
+	KnownTypes        []*KnownType   `json:"knownTypes"`
+	KubernetesVersion string         `json:"kubernetesVersion"`
+	LinkMappings      []*LinkMapping `json:"linkMappings"`
 }
 
 type KnownType struct {
@@ -62,6 +63,12 @@ type KnownType struct {
 	Link    string `json:"link"`
 }
 
+type LinkMapping struct {
+	URL  string `json:"url"`
+	Link string `json:"link"`
+	Text string `json:"text"`
+}
+
 const (
 	OutputModeSingle = "single"
 	OutputModeGroup  = "group"
diff --git a/renderer/markdown.go b/renderer/markdown.go
index a270c10..9ded306 100644
--- a/renderer/markdown.go
+++ b/renderer/markdown.go
@@ -72,6 +72,7 @@ func (m *MarkdownRenderer) ToFuncMap() template.FuncMap {
 		"RenderLocalLink":    m.RenderLocalLink,
 		"RenderType":         m.RenderType,
 		"RenderTypeLink":     m.RenderTypeLink,
+		"RewriteLinks":       m.RewriteLinks,
 		"SafeID":             m.SafeID,
 		"ShouldRenderType":   m.ShouldRenderType,
 		"TypeID":             m.TypeID,
@@ -148,10 +149,22 @@ func (m *MarkdownRenderer) RenderGVLink(gv types.GroupVersionDetails) string {
 	return m.RenderLocalLink(gv.GroupVersionString())
 }
 
+func (m *MarkdownRenderer) RewriteLinks(text string) string {
+	if m == nil || m.conf == nil {
+		return text
+	}
+	for _, lm := range m.conf.Render.LinkMappings {
+		text = strings.ReplaceAll(text, lm.URL, m.RenderExternalLink(lm.Link, lm.Text))
+	}
+	return text
+}
+
 func (m *MarkdownRenderer) RenderFieldDoc(text string) string {
+	out := m.RewriteLinks(text)
+
 	// Escape the pipe character, which has special meaning for Markdown as a way to format tables
 	// so that including | in a comment does not result in wonky tables.
-	out := strings.ReplaceAll(text, "|", "\\|")
+	out = strings.ReplaceAll(out, "|", "\\|")
 
 	// Escape the curly bracket character.
 	out = strings.ReplaceAll(out, "{", "\\{")
diff --git a/renderer/markdown_test.go b/renderer/markdown_test.go
index ddd1063..2760e1c 100644
--- a/renderer/markdown_test.go
+++ b/renderer/markdown_test.go
@@ -35,6 +35,119 @@ func newTestConfig(t *testing.T) *config.Config {
 	return conf
 }
 
+func TestMarkdownRenderer_RewriteLinks(t *testing.T) {
+	conf := &config.Config{
+		Render: config.RenderConfig{
+			LinkMappings: []*config.LinkMapping{
+				{
+					URL:  "https://example.com/old",
+					Link: "docs-content://new/page.md",
+					Text: "New page",
+				},
+				{
+					URL:  "https://example.com/other",
+					Link: "kibana://reference/other.md",
+					Text: "Other",
+				},
+			},
+		},
+	}
+	r := &MarkdownRenderer{conf: conf}
+
+	tests := []struct {
+		name     string
+		renderer *MarkdownRenderer
+		text     string
+		want     string
+	}{
+		{
+			name:     "single substitution",
+			renderer: r,
+			text:     "See https://example.com/old for details.",
+			want:     "See [New page](docs-content://new/page.md) for details.",
+		},
+		{
+			name:     "multiple substitutions",
+			renderer: r,
+			text:     "See https://example.com/old and https://example.com/other.",
+			want:     "See [New page](docs-content://new/page.md) and [Other](kibana://reference/other.md).",
+		},
+		{
+			name:     "no match leaves text unchanged",
+			renderer: r,
+			text:     "See https://example.com/unmapped for details.",
+			want:     "See https://example.com/unmapped for details.",
+		},
+		{
+			name:     "no mappings configured",
+			renderer: &MarkdownRenderer{conf: &config.Config{}},
+			text:     "See https://example.com/old for details.",
+			want:     "See https://example.com/old for details.",
+		},
+		{
+			name:     "nil config",
+			renderer: &MarkdownRenderer{conf: nil},
+			text:     "See https://example.com/old for details.",
+			want:     "See https://example.com/old for details.",
+		},
+		{
+			name:     "nil renderer",
+			renderer: nil,
+			text:     "See https://example.com/old for details.",
+			want:     "See https://example.com/old for details.",
+		},
+		{
+			name:     "multiple occurrences of the same URL are all rewritten",
+			renderer: r,
+			text:     "See https://example.com/old and again https://example.com/old.",
+			want:     "See [New page](docs-content://new/page.md) and again [New page](docs-content://new/page.md).",
+		},
+		{
+			name: "longer URL listed first wins over shorter prefix",
+			renderer: &MarkdownRenderer{conf: &config.Config{
+				Render: config.RenderConfig{
+					LinkMappings: []*config.LinkMapping{
+						{URL: "https://example.com/old-page", Link: "docs-content://new/page.md", Text: "New page"},
+						{URL: "https://example.com/old", Link: "docs-content://other.md", Text: "Other"},
+					},
+				},
+			}},
+			text: "See https://example.com/old-page for details.",
+			want: "See [New page](docs-content://new/page.md) for details.",
+		},
+		{
+			name:     "URL inside an existing Markdown link produces nested output",
+			renderer: r,
+			text:     "See [the page](https://example.com/old) for details.",
+			want:     "See [the page]([New page](docs-content://new/page.md)) for details.",
+		},
+	}
+
+	for _, tt := range tests {
+		t.Run(tt.name, func(t *testing.T) {
+			assert.Equal(t, tt.want, tt.renderer.RewriteLinks(tt.text))
+		})
+	}
+}
+
+func TestMarkdownRenderer_RenderFieldDoc_appliesLinkMappings(t *testing.T) {
+	conf := &config.Config{
+		Render: config.RenderConfig{
+			LinkMappings: []*config.LinkMapping{
+				{
+					URL:  "https://example.com/old",
+					Link: "docs-content://new/page.md",
+					Text: "New page",
+				},
+			},
+		},
+	}
+	r := &MarkdownRenderer{conf: conf}
+
+	got := r.RenderFieldDoc("See https://example.com/old for details.")
+	assert.Equal(t, "See [New page](docs-content://new/page.md) for details.", got)
+}
+
 func TestMarkdownRenderer_TemplateValue(t *testing.T) {
 	tests := []struct {
 		name     string
diff --git a/templates/markdown/type.tpl b/templates/markdown/type.tpl
index 7d89d04..f8b91a6 100644
--- a/templates/markdown/type.tpl
+++ b/templates/markdown/type.tpl
@@ -6,7 +6,7 @@
 
 {{ if $type.IsAlias }}_Underlying type:_ _{{ markdownRenderTypeLink $type.UnderlyingType  }}_{{ end }}
 
-{{ $type.Doc }}
+{{ markdownRewriteLinks $type.Doc }}
 
 {{ if $type.Validation -}}
 _Validation:_
diff --git a/test/api/v1/guestbook_types.go b/test/api/v1/guestbook_types.go
index 8eb71bc..d89557c 100644
--- a/test/api/v1/guestbook_types.go
+++ b/test/api/v1/guestbook_types.go
@@ -121,9 +121,9 @@ const (
 // +kubebuilder:validation:Minimum=1
 type PositiveInt int
 
-// GuestbookEntry defines an entry in a guest book.
+// GuestbookEntry defines an entry in a guest book. See https://example.com/old-page for more.
 type GuestbookEntry struct {
-	// Name of the guest (pipe | should be escaped)
+	// Name of the guest (pipe | should be escaped). See https://example.com/old-page for naming guidance.
 	// +kubebuilder:validation:Required
 	// +kubebuilder:validation:MaxLength=80
 	// +kubebuilder:validation:Pattern=`0*[a-z0-9]*[a-z]*[0-9]`
diff --git a/test/config.yaml b/test/config.yaml
index 2ebede7..4f655e2 100644
--- a/test/config.yaml
+++ b/test/config.yaml
@@ -18,3 +18,7 @@ render:
     - name: SecretObjectReference
       package: sigs.k8s.io/gateway-api/apis/v1beta1
       link: https://gateway-api.sigs.k8s.io/references/spec/#gateway.networking.k8s.io/v1beta1.SecretObjectReference
+  linkMappings:
+    - url: https://example.com/old-page
+      link: docs-content://new/page.md
+      text: New page
diff --git a/test/expected.asciidoc b/test/expected.asciidoc
index dff065f..c979eaf 100644
--- a/test/expected.asciidoc
+++ b/test/expected.asciidoc
@@ -148,7 +148,7 @@ Guestbook is the Schema for the guestbooks API.
 
 
 
-GuestbookEntry defines an entry in a guest book.
+GuestbookEntry defines an entry in a guest book. See https://example.com/old-page for more.
 
 
 
@@ -160,7 +160,7 @@ GuestbookEntry defines an entry in a guest book.
 [cols="20a,50a,15a,15a", options="header"]
 |===
 | Field | Description | Default | Validation
-| *`name`* __string__ | Name of the guest (pipe \| should be escaped) + |  | MaxLength: 80 +
+| *`name`* __string__ | Name of the guest (pipe \| should be escaped). See https://example.com/old-page for naming guidance. + |  | MaxLength: 80 +
 Pattern: `0\*[a-z0-9]*[a-z]*[0-9]` +
 Required: \{} +
 
diff --git a/test/expected.md b/test/expected.md
index 538adf6..0b7de7f 100644
--- a/test/expected.md
+++ b/test/expected.md
@@ -118,7 +118,7 @@ _Appears in:_
 
 
 
-GuestbookEntry defines an entry in a guest book.
+GuestbookEntry defines an entry in a guest book. See [New page](docs-content://new/page.md) for more.
 
 
 
@@ -127,7 +127,7 @@ _Appears in:_
 
 | Field | Description | Default | Validation |
 | --- | --- | --- | --- |
-| `name` _string_ | Name of the guest (pipe \| should be escaped) |  | MaxLength: 80 <br />Pattern: `0*[a-z0-9]*[a-z]*[0-9]` <br />Required: \{\} <br /> |
+| `name` _string_ | Name of the guest (pipe \| should be escaped). See [New page](docs-content://new/page.md) for naming guidance. |  | MaxLength: 80 <br />Pattern: `0*[a-z0-9]*[a-z]*[0-9]` <br />Required: \{\} <br /> |
 | `tags` _string array_ | Tags of the entry. |  | items:Pattern: `[a-z]*` <br /> |
 | `time` _[Time](https://kubernetes.io/docs/reference/generated/kubernetes-api/v1.25/#time-v1-meta)_ | Time of entry |  |  |
 | `comment` _string_ | Comment by guest. This can be a multi-line comment.<br />Like this one.<br />Now let's test a list:<br />* a<br />* b<br />Another isolated comment.<br />Looks good? |  | Pattern: `0*[a-z0-9]*[a-z]*[0-9]*\|\s` <br /> |
diff --git a/test/hide.md b/test/hide.md
index d274f96..191fbdf 100644
--- a/test/hide.md
+++ b/test/hide.md
@@ -119,7 +119,7 @@ _Appears in:_
 
 
 
-GuestbookEntry defines an entry in a guest book.
+GuestbookEntry defines an entry in a guest book. See [New page](docs-content://new/page.md) for more.
 
 
 
@@ -128,7 +128,7 @@ _Appears in:_
 
 | Field | Description | Default | Validation |
 | --- | --- | --- | --- |
-| `name` _string_ | Name of the guest (pipe \| should be escaped) |  | MaxLength: 80 <br />Pattern: `0*[a-z0-9]*[a-z]*[0-9]` <br />Required: \{\} <br /> |
+| `name` _string_ | Name of the guest (pipe \| should be escaped). See [New page](docs-content://new/page.md) for naming guidance. |  | MaxLength: 80 <br />Pattern: `0*[a-z0-9]*[a-z]*[0-9]` <br />Required: \{\} <br /> |
 | `tags` _string array_ | Tags of the entry. |  | items:Pattern: `[a-z]*` <br /> |
 | `time` _[Time](https://kubernetes.io/docs/reference/generated/kubernetes-api/v1.25/#time-v1-meta)_ | Time of entry |  |  |
 | `comment` _string_ | Comment by guest. This can be a multi-line comment.<br />Like this one.<br />Now let's test a list:<br />* a<br />* b<br />Another isolated comment.<br />Looks good? |  | Pattern: `0*[a-z0-9]*[a-z]*[0-9]*\|\s` <br /> |
diff --git a/test/templates/markdown/type.tpl b/test/templates/markdown/type.tpl
index 1ef5d62..61f39e0 100644
--- a/test/templates/markdown/type.tpl
+++ b/test/templates/markdown/type.tpl
@@ -6,7 +6,7 @@
 
 {{ if $type.IsAlias }}_Underlying type:_ _{{ markdownRenderTypeLink $type.UnderlyingType  }}_{{ end }}
 
-{{ $type.Doc }}
+{{ markdownRewriteLinks $type.Doc }}
 
 {{ if $type.Validation -}}
 _Validation:_