diff --git a/docs/.ruby-version b/docs/.ruby-version
index 3a8d0124..7bde84d0 100644
--- a/docs/.ruby-version
+++ b/docs/.ruby-version
@@ -1 +1 @@
-ruby-3.0.4
\ No newline at end of file
+ruby-3.1.2
diff --git a/docs/Gemfile.lock b/docs/Gemfile.lock
index a6a6e852..0758d4cd 100644
--- a/docs/Gemfile.lock
+++ b/docs/Gemfile.lock
@@ -133,6 +133,7 @@ PLATFORMS
   arm64-darwin-21
   arm64-darwin-22
   arm64-darwin-23
+  arm64-darwin-24
   x86_64-linux
 
 DEPENDENCIES
diff --git a/tests/rails/Gemfile.lock b/tests/rails/Gemfile.lock
index a7e0b421..a2a2e0c2 100644
--- a/tests/rails/Gemfile.lock
+++ b/tests/rails/Gemfile.lock
@@ -276,7 +276,7 @@ GEM
     y-rb_actioncable (0.1.7)
       rails (>= 7.0.4)
       y-rb (>= 0.4.5)
-    zeitwerk (2.7.1)
+    zeitwerk (2.6.18)
 
 PLATFORMS
   arm64-darwin-21
diff --git a/tests/rails/app/frontend/controllers/markdown_link.js b/tests/rails/app/frontend/controllers/markdown_link.js
new file mode 100644
index 00000000..48f90c3c
--- /dev/null
+++ b/tests/rails/app/frontend/controllers/markdown_link.js
@@ -0,0 +1,118 @@
+/**
+ * Adapted from Typist's extension: https://github.com/Doist/typist/blob/main/src/extensions/rich-text/rich-text-link.ts
+ */
+import { InputRule, markInputRule, markPasteRule, PasteRule } from '@tiptap/core'
+import { Link } from '@tiptap/extension-link'
+// import type { LinkOptions } from '@tiptap/extension-link'
+
+/**
+ * The input regex for Markdown links with title support, and multiple quotation marks (required
+ * in case the `Typography` extension is being included).
+ */
+const inputRegex = /(?:^|\s)\[([^\]]*)?\]\((\S+)(?: ["“](.+)["”])?\)$/i
+
+/**
+ * The paste regex for Markdown links with title support, and multiple quotation marks (required
+ * in case the `Typography` extension is being included).
+ */
+const pasteRegex = /(?:^|\s)\[([^\]]*)?\]\((\S+)(?: ["“](.+)["”])?\)/gi
+
+/**
+ * Input rule built specifically for the `Link` extension, which ignores the auto-linked URL in
+ * parentheses (e.g., `(https://doist.dev)`).
+ *
+ * @see https://github.com/ueberdosis/tiptap/discussions/1865
+ */
+function linkInputRule(config) {
+  const defaultMarkInputRule = markInputRule(config)
+
+  return new InputRule({
+    find: config.find,
+    handler(props) {
+      const { tr } = props.state
+
+      defaultMarkInputRule.handler(props)
+      tr.setMeta('preventAutolink', true)
+    },
+  })
+}
+
+/**
+ * Paste rule built specifically for the `Link` extension, which ignores the auto-linked URL in
+ * parentheses (e.g., `(https://doist.dev)`). This extension was inspired from the multiple
+ * implementations found in a Tiptap discussion at GitHub.
+ *
+ * @see https://github.com/ueberdosis/tiptap/discussions/1865
+ */
+function linkPasteRule(config) {
+  const defaultMarkPasteRule = markPasteRule(config)
+
+  return new PasteRule({
+    find: config.find,
+    handler(props) {
+      const { tr } = props.state
+
+      defaultMarkPasteRule.handler(props)
+      tr.setMeta('preventAutolink', true)
+    },
+  })
+}
+
+/**
+ * Custom extension that extends the built-in `Link` extension to add additional input/paste rules
+ * for converting the Markdown link syntax (i.e. `[Doist](https://doist.com)`) into links, and also
+ * adds support for the `title` attribute.
+ */
+export const MarkdownLink = Link.extend({
+  inclusive: false,
+  addOptions() {
+    return {
+      ...this.parent?.(),
+      openOnClick: 'whenNotEditable',
+    }
+  },
+  addAttributes() {
+    return {
+      ...this.parent?.(),
+      title: {
+        default: null,
+      },
+    }
+  },
+  addInputRules() {
+    return [
+      linkInputRule({
+        find: inputRegex,
+        type: this.type,
+
+        // We need to use `pop()` to remove the last capture groups from the match to
+        // satisfy Tiptap's `markPasteRule` expectation of having the content as the last
+        // capture group in the match (this makes the attribute order important)
+        getAttributes(match) {
+          return {
+            title: match.pop()?.trim(),
+            href: match.pop()?.trim(),
+          }
+        },
+      }),
+    ]
+  },
+  addPasteRules() {
+    return [
+      linkPasteRule({
+        find: pasteRegex,
+        type: this.type,
+
+        // We need to use `pop()` to remove the last capture groups from the match to
+        // satisfy Tiptap's `markInputRule` expectation of having the content as the last
+        // capture group in the match (this makes the attribute order important)
+        getAttributes(match) {
+          return {
+            title: match.pop()?.trim(),
+            href: match.pop()?.trim(),
+          }
+        },
+      }),
+    ]
+  },
+})
diff --git a/tests/rails/app/frontend/entrypoints/application.js b/tests/rails/app/frontend/entrypoints/application.js
index 3d1dd230..9cb2b622 100644
--- a/tests/rails/app/frontend/entrypoints/application.js
+++ b/tests/rails/app/frontend/entrypoints/application.js
@@ -8,6 +8,7 @@ import "trix/dist/trix.css";
 import { Application } from "@hotwired/stimulus"
 import EmbedController from "../controllers/embed_controller.js"
 import TipTapMirrorController from "../controllers/tip_tap_mirror_controller.js"
+import { MarkdownLink } from "../controllers/markdown_link.js"
 window.Stimulus = Application.start()
 window.Stimulus.debug = true
 Stimulus.register("embed", EmbedController)
@@ -32,6 +33,11 @@ ActiveStorage.start()
   if (trixHtmlMirror) Prism.highlightElement(trixHtmlMirror)
   if (tipTapHtmlMirror) Prism.highlightElement(tipTapHtmlMirror)
 
+  const rhinoEditor = document.querySelector("rhino-editor[input=y]")
+  rhinoEditor.addExtensions(
+    MarkdownLink,
+  )
+
   const escapeHTML = (str) => {
     const p = document.createElement("p");
     p.appendChild(document.createTextNode(str));