diff --git a/src/renderer/src/components/editor/raw-markdown-html.ts b/src/renderer/src/components/editor/raw-markdown-html.ts
index cde5311e80b..d07eb182e63 100644
--- a/src/renderer/src/components/editor/raw-markdown-html.ts
+++ b/src/renderer/src/components/editor/raw-markdown-html.ts
@@ -7,7 +7,10 @@ import type {
   RichMarkdownSourceKind,
   RichMarkdownSourceTransport
 } from './rich-markdown-source-transport'
-import { isReservedRichMarkdownTransportBody } from './rich-markdown-source-transport'
+import {
+  isReservedRichMarkdownTransportBody,
+  skipInlineTransportStartScan
+} from './rich-markdown-source-transport'
 import { matchHtmlSuperscriptLinkSource } from './rich-markdown-html-superscript-link-source'
 
 const INLINE_HTML_PATTERN = /^<!--[\s\S]*?-->|^<\/?[A-Za-z][\w.:-]*(?:\s[^<>]*?)?\/?>/
@@ -273,7 +276,7 @@ function createRawSourceNode({
     markdownTokenizer: {
       name,
       level: inline ? 'inline' : 'block',
-      start: transport.startFor(kind),
+      start: inline ? skipInlineTransportStartScan : transport.startFor(kind),
       tokenize(src) {
         const matched = transport.match(src, kind)
         if (!matched) {
diff --git a/src/renderer/src/components/editor/rich-markdown-doc-link.ts b/src/renderer/src/components/editor/rich-markdown-doc-link.ts
index e2245ec472a..1ae68d44bfe 100644
--- a/src/renderer/src/components/editor/rich-markdown-doc-link.ts
+++ b/src/renderer/src/components/editor/rich-markdown-doc-link.ts
@@ -11,6 +11,7 @@ import {
 } from './markdown-doc-links'
 import {
   isReservedRichMarkdownTransportBody,
+  skipInlineTransportStartScan,
   type RichMarkdownSourceTransport
 } from './rich-markdown-source-transport'
 import { renderRichMarkdownDocLinkHtml } from './rich-markdown-doc-link-dom'
@@ -126,7 +127,7 @@ export function createMarkdownDocLink(transport: RichMarkdownSourceTransport) {
     markdownTokenizer: {
       name: 'markdownDocLink',
       level: 'inline',
-      start: transport.startFor('document-link'),
+      start: skipInlineTransportStartScan,
       tokenize(src: string) {
         const matched = transport.match(src, 'document-link')
         if (!matched) {
diff --git a/src/renderer/src/components/editor/rich-markdown-html-superscript-link.ts b/src/renderer/src/components/editor/rich-markdown-html-superscript-link.ts
index da3f919fd3b..a60a6e9c777 100644
--- a/src/renderer/src/components/editor/rich-markdown-html-superscript-link.ts
+++ b/src/renderer/src/components/editor/rich-markdown-html-superscript-link.ts
@@ -1,5 +1,8 @@
 import { Node } from '@tiptap/core'
-import type { RichMarkdownSourceTransport } from './rich-markdown-source-transport'
+import {
+  skipInlineTransportStartScan,
+  type RichMarkdownSourceTransport
+} from './rich-markdown-source-transport'
 import {
   HTML_SUPERSCRIPT_LINK_SOURCE_LIMIT,
   parseHtmlSuperscriptLinkSource,
@@ -41,7 +44,7 @@ export function createRichMarkdownHtmlSuperscriptLink(
     markdownTokenizer: {
       name: 'richMarkdownHtmlSuperscriptLink',
       level: 'inline',
-      start: transport.startFor('html-superscript-link'),
+      start: skipInlineTransportStartScan,
       tokenize(source) {
         const matched = transport.match(source, 'html-superscript-link')
         if (!matched) {
diff --git a/src/renderer/src/components/editor/rich-markdown-inline-source-tokenization.test.ts b/src/renderer/src/components/editor/rich-markdown-inline-source-tokenization.test.ts
new file mode 100644
index 00000000000..bc86bf4011a
--- /dev/null
+++ b/src/renderer/src/components/editor/rich-markdown-inline-source-tokenization.test.ts
@@ -0,0 +1,22 @@
+// @vitest-environment happy-dom
+
+import { describe, expect, it } from 'vitest'
+import { getRichMarkdownRoundTripOutput } from './markdown-round-trip'
+
+describe('inline source tokens at text boundaries', () => {
+  for (const prefix of ['plain ', '中文', '(', '*emphasis* ']) {
+    it.each(['<kbd>Key</kbd>', '[[note|Label]]', '<sup><a href="./ref.md">[12]</a></sup>'])(
+      `recognizes %j after ${JSON.stringify(prefix)}`,
+      (fragment) => {
+        const source = `${prefix}${fragment} suffix`
+        expect(getRichMarkdownRoundTripOutput(source)).toBe(source)
+      }
+    )
+  }
+
+  it('preserves a large paragraph with dense malformed links and embedded source tokens', () => {
+    const prose = 'Text [[]] with a blank [[alias|]] and ordinary prose. '.repeat(1000)
+    const source = `${prose}<kbd>Key</kbd> [[note|Label]] ${prose.trim()}`
+    expect(getRichMarkdownRoundTripOutput(source)).toBe(source)
+  })
+})
diff --git a/src/renderer/src/components/editor/rich-markdown-source-transport.ts b/src/renderer/src/components/editor/rich-markdown-source-transport.ts
index 94369d6e667..138ffb1ad91 100644
--- a/src/renderer/src/components/editor/rich-markdown-source-transport.ts
+++ b/src/renderer/src/components/editor/rich-markdown-source-transport.ts
@@ -15,6 +15,11 @@ const TRANSPORT_BODY_PATTERN =
   /^ORCA_RICH_MD:[a-f0-9]{32}:(?:literal|inline-html|block-html|document-link|html-superscript-link):/
 const LEGACY_PREFIXES = ['ORCA_RAW_HTML_INLINE:', 'ORCA_RAW_HTML_BLOCK:', 'ORCA_DOC_LINK:'] as const
 
+export function skipInlineTransportStartScan(): number {
+  // Marked already stops text at `[`, so inline envelopes need no suffix scan.
+  return -1
+}
+
 export type RichMarkdownSourceTransport = {
   readonly key: string
   readonly authoredPrefix: string