diff --git a/src/components/Editor.tsx b/src/components/Editor.tsx
index c8402f95..6bb3300c 100644
--- a/src/components/Editor.tsx
+++ b/src/components/Editor.tsx
@@ -20,6 +20,7 @@ import {
   resolveRawModeContent,
 } from './editorRawModeSync'
 import { useRawModeWithFlush } from './useRawModeWithFlush'
+import { useFilenameAutolinkGuard } from './useFilenameAutolinkGuard'
 import './Editor.css'
 import './EditorTheme.css'
 
@@ -167,6 +168,7 @@ function useEditorSetup({
     schema,
     uploadFile: (file: File) => uploadImageFile(file, vaultPathRef.current),
   })
+  useFilenameAutolinkGuard(editor)
   const activeTab = tabs.find((t) => t.entry.path === activeTabPath) ?? null
   const {
     rawMode,
diff --git a/src/components/useFilenameAutolinkGuard.ts b/src/components/useFilenameAutolinkGuard.ts
new file mode 100644
index 00000000..d7e5a960
--- /dev/null
+++ b/src/components/useFilenameAutolinkGuard.ts
@@ -0,0 +1,132 @@
+import { useEffect } from 'react'
+import type { useCreateBlockNote } from '@blocknote/react'
+import { shouldStripAutoLinkedLocalFileMark } from '../utils/editorLinkAutolink'
+
+const FILENAME_AUTOLINK_GUARD_META = 'tolaria-filename-autolink-guard'
+
+type TiptapLinkMark = {
+  attrs?: {
+    href?: string
+  }
+  type: unknown
+}
+
+type TiptapTextNode = {
+  isText?: boolean
+  marks?: TiptapLinkMark[]
+  nodeSize: number
+  text?: string | null
+}
+
+function hasTextContent(node: TiptapTextNode) {
+  return Boolean(node.isText && node.text && node.marks?.length)
+}
+
+function isAccidentalFilenameLinkMark(
+  mark: TiptapLinkMark,
+  linkMarkType: unknown,
+  text: string,
+) {
+  if (mark.type !== linkMarkType) {
+    return false
+  }
+
+  if (typeof mark.attrs?.href !== 'string') {
+    return false
+  }
+
+  return shouldStripAutoLinkedLocalFileMark({
+    href: { raw: mark.attrs.href },
+    text: { raw: text },
+  })
+}
+
+function hasEditorEventApi(
+  tiptap: ReturnType<typeof useCreateBlockNote>['_tiptapEditor'] | undefined,
+) {
+  return Boolean(tiptap && typeof tiptap.on === 'function' && typeof tiptap.off === 'function')
+}
+
+function collectAccidentalFilenameLinkRanges(editor: ReturnType<typeof useCreateBlockNote>) {
+  const linkMarkType = editor._tiptapEditor?.schema?.marks?.link
+  if (!linkMarkType) {
+    return []
+  }
+
+  const ranges: Array<{ from: number; to: number }> = []
+  editor._tiptapEditor.state.doc.descendants((node: TiptapTextNode, pos: number) => {
+    if (!hasTextContent(node)) {
+      return
+    }
+
+    const hasAccidentalFilenameLink = node.marks.some((mark) => (
+      isAccidentalFilenameLinkMark(mark, linkMarkType, node.text ?? '')
+    ))
+
+    if (hasAccidentalFilenameLink) {
+      ranges.push({ from: pos, to: pos + node.nodeSize })
+    }
+  })
+
+  return ranges
+}
+
+function shouldSkipGuardRun(
+  applyingGuard: boolean,
+  transaction: { docChanged?: boolean; getMeta: (key: string) => unknown },
+) {
+  return (
+    applyingGuard
+    || !transaction.docChanged
+    || transaction.getMeta(FILENAME_AUTOLINK_GUARD_META)
+  )
+}
+
+function removeLinkRanges(
+  editor: ReturnType<typeof useCreateBlockNote>,
+  ranges: Array<{ from: number; to: number }>,
+) {
+  const tr = editor._tiptapEditor.state.tr
+  for (const range of ranges) {
+    tr.removeMark(range.from, range.to, editor._tiptapEditor.schema.marks.link)
+  }
+
+  return tr
+}
+
+export function useFilenameAutolinkGuard(editor: ReturnType<typeof useCreateBlockNote>) {
+  useEffect(() => {
+    const tiptap = editor._tiptapEditor
+    if (!hasEditorEventApi(tiptap)) {
+      return
+    }
+
+    let applyingGuard = false
+    const stripAccidentalFilenameAutolinks = ({ transaction }: { transaction: { docChanged?: boolean; getMeta: (key: string) => unknown } }) => {
+      if (shouldSkipGuardRun(applyingGuard, transaction)) {
+        return
+      }
+
+      const ranges = collectAccidentalFilenameLinkRanges(editor)
+      if (ranges.length === 0) {
+        return
+      }
+
+      const tr = removeLinkRanges(editor, ranges)
+      if (!tr.docChanged) {
+        return
+      }
+
+      tr.setMeta(FILENAME_AUTOLINK_GUARD_META, true)
+      applyingGuard = true
+      tiptap.view.dispatch(tr)
+      applyingGuard = false
+    }
+
+    tiptap.on('update', stripAccidentalFilenameAutolinks)
+
+    return () => {
+      tiptap.off('update', stripAccidentalFilenameAutolinks)
+    }
+  }, [editor])
+}
diff --git a/src/utils/editorLinkAutolink.test.ts b/src/utils/editorLinkAutolink.test.ts
new file mode 100644
index 00000000..cd0fe68a
--- /dev/null
+++ b/src/utils/editorLinkAutolink.test.ts
@@ -0,0 +1,62 @@
+import { describe, expect, it } from 'vitest'
+import {
+  looksLikeLocalFileReference,
+  shouldStripAutoLinkedLocalFileMark,
+  shouldAutoLinkTolariaHref,
+} from './editorLinkAutolink'
+
+describe('looksLikeLocalFileReference', () => {
+  it('treats bare filenames with file extensions as local file references', () => {
+    expect(looksLikeLocalFileReference({ raw: 'AGENTS.md' })).toBe(true)
+    expect(looksLikeLocalFileReference({ raw: 'README.txt' })).toBe(true)
+  })
+
+  it('treats local path-like filenames as local file references', () => {
+    expect(looksLikeLocalFileReference({ raw: 'docs/README.md' })).toBe(true)
+    expect(looksLikeLocalFileReference({ raw: './docs/README.md' })).toBe(true)
+    expect(looksLikeLocalFileReference({ raw: '/vault/README.md' })).toBe(true)
+  })
+
+  it('does not classify domain-based urls as local file references', () => {
+    expect(looksLikeLocalFileReference({ raw: 'https://example.com/README.md' })).toBe(false)
+    expect(looksLikeLocalFileReference({ raw: 'example.com/README.md' })).toBe(false)
+    expect(looksLikeLocalFileReference({ raw: 'www.example.com/README.md' })).toBe(false)
+  })
+})
+
+describe('shouldAutoLinkTolariaHref', () => {
+  it('rejects plain filename-like text', () => {
+    expect(shouldAutoLinkTolariaHref({ raw: 'AGENTS.md' })).toBe(false)
+    expect(shouldAutoLinkTolariaHref({ raw: 'docs/README.md' })).toBe(false)
+  })
+
+  it('keeps normal url-like values eligible for autolinking', () => {
+    expect(shouldAutoLinkTolariaHref({ raw: 'https://example.com/docs' })).toBe(true)
+    expect(shouldAutoLinkTolariaHref({ raw: 'example.com' })).toBe(true)
+    expect(shouldAutoLinkTolariaHref({ raw: 'example.com/README.md' })).toBe(true)
+  })
+})
+
+describe('shouldStripAutoLinkedLocalFileMark', () => {
+  it('strips accidental link marks that mirror local file text', () => {
+    expect(shouldStripAutoLinkedLocalFileMark({
+      href: { raw: 'https://AGENTS.md' },
+      text: { raw: 'AGENTS.md' },
+    })).toBe(true)
+    expect(shouldStripAutoLinkedLocalFileMark({
+      href: { raw: 'https://docs/README.md' },
+      text: { raw: 'docs/README.md' },
+    })).toBe(true)
+  })
+
+  it('keeps intentional external links', () => {
+    expect(shouldStripAutoLinkedLocalFileMark({
+      href: { raw: 'https://example.com/docs' },
+      text: { raw: 'Tolaria Docs' },
+    })).toBe(false)
+    expect(shouldStripAutoLinkedLocalFileMark({
+      href: { raw: 'https://example.com/agents' },
+      text: { raw: 'AGENTS.md' },
+    })).toBe(false)
+  })
+})
diff --git a/src/utils/editorLinkAutolink.ts b/src/utils/editorLinkAutolink.ts
new file mode 100644
index 00000000..4baa7e83
--- /dev/null
+++ b/src/utils/editorLinkAutolink.ts
@@ -0,0 +1,143 @@
+const FILE_LIKE_EXTENSION_PATTERN =
+  /\.(?:md|markdown|txt|ya?ml|json|toml|csv|tsv|pdf|png|jpe?g|gif|svg|webp|avif|mp3|wav|ogg|mp4|mov|zip|tar|gz|tsx?|jsx?|cjs|mjs|rs|py|sh|css|html?)$/i
+
+const EXPLICIT_PROTOCOL_PATTERN = /^[a-z][a-z0-9+.-]*:\/\//i
+const MAYBE_PROTOCOL_PATTERN = /^[a-z][a-z0-9+.-]*:/i
+const LOCAL_PATH_PREFIX_PATTERN = /^(?:\.{1,2}\/|~\/|\/)/
+const IPV4_HOST_PATTERN = /^\d{1,3}(\.\d{1,3}){3}$/
+const WINDOWS_PATH_SEPARATOR = '\\'
+const WWW_PREFIX = 'www.'
+
+export type LinkValue = {
+  raw: string
+}
+
+export type LinkMarkCandidate = {
+  href: LinkValue
+  text: LinkValue
+}
+
+function withRaw(raw: string): LinkValue {
+  return { raw }
+}
+
+function stripUrlDecorators(value: LinkValue) {
+  return withRaw(value.raw.split(/[?#]/, 1)[0] ?? value.raw)
+}
+
+function stripProtocol(value: LinkValue) {
+  return withRaw(value.raw.replace(/^[a-z][a-z0-9+.-]*:\/\//i, ''))
+}
+
+function isExplicitProtocolUrl(value: LinkValue) {
+  return EXPLICIT_PROTOCOL_PATTERN.test(value.raw)
+}
+
+function isMaybeProtocolUrl(value: LinkValue) {
+  return MAYBE_PROTOCOL_PATTERN.test(value.raw)
+}
+
+function hasWindowsPathSeparator(value: LinkValue) {
+  return value.raw.includes(WINDOWS_PATH_SEPARATOR)
+}
+
+function hasPathSeparator(value: LinkValue) {
+  return value.raw.includes('/')
+}
+
+function startsWithWebHostPrefix(value: LinkValue) {
+  return value.raw.startsWith(WWW_PREFIX)
+}
+
+function firstPathSegment(value: LinkValue) {
+  return value.raw.split('/', 1)[0] ?? value.raw
+}
+
+function isDomainLikePath(value: LinkValue) {
+  return firstPathSegment(value).includes('.')
+}
+
+function hostnameFromUrlLikeValue(value: LinkValue) {
+  const withoutUserinfo = value.raw.includes('@') ? value.raw.split('@').pop() ?? value.raw : value.raw
+  return withoutUserinfo.split(/[/?#:]/, 1)[0] ?? withoutUserinfo
+}
+
+function isExplicitWebUrl(value: LinkValue) {
+  return isExplicitProtocolUrl(value) || startsWithWebHostPrefix(value)
+}
+
+function isSingleSegmentValue(value: LinkValue) {
+  return !hasPathSeparator(value)
+}
+
+function isLocalPathPrefix(value: LinkValue) {
+  return LOCAL_PATH_PREFIX_PATTERN.test(value.raw)
+}
+
+function isPathLikeFileReference(value: LinkValue) {
+  return hasPathSeparator(value) && !isDomainLikePath(value)
+}
+
+function hasBareProtocolPrefix(value: LinkValue) {
+  return isMaybeProtocolUrl(value) && !value.raw.includes('@')
+}
+
+function hostnameHasTld(hostname: string) {
+  return hostname.includes('.')
+}
+
+function normalizeInput(value: LinkValue) {
+  return stripUrlDecorators(withRaw(value.raw.trim()))
+}
+
+export function looksLikeLocalFileReference(value: LinkValue) {
+  const normalized = normalizeInput(value)
+  if (!normalized.raw) return false
+
+  if (isLocalPathPrefix(normalized) || hasWindowsPathSeparator(normalized)) {
+    return true
+  }
+
+  if (!FILE_LIKE_EXTENSION_PATTERN.test(normalized.raw)) {
+    return false
+  }
+
+  if (isExplicitWebUrl(normalized)) {
+    return false
+  }
+
+  if (isSingleSegmentValue(normalized)) {
+    return true
+  }
+
+  return isPathLikeFileReference(normalized)
+}
+
+export function shouldAutoLinkTolariaHref(url: LinkValue) {
+  if (looksLikeLocalFileReference(url)) {
+    return false
+  }
+
+  if (isExplicitProtocolUrl(url) || hasBareProtocolPrefix(url)) {
+    return true
+  }
+
+  const hostname = hostnameFromUrlLikeValue(url)
+  if (IPV4_HOST_PATTERN.test(hostname)) {
+    return false
+  }
+
+  return hostnameHasTld(hostname)
+}
+
+export function shouldStripAutoLinkedLocalFileMark(mark: LinkMarkCandidate) {
+  const normalizedText = normalizeInput(mark.text)
+  if (!looksLikeLocalFileReference(normalizedText)) {
+    return false
+  }
+
+  const normalizedHref = stripUrlDecorators(
+    stripProtocol(normalizeInput(mark.href)),
+  )
+  return normalizedHref.raw === normalizedText.raw
+}
diff --git a/tests/smoke/plain-filename-autolink.spec.ts b/tests/smoke/plain-filename-autolink.spec.ts
new file mode 100644
index 00000000..ef659e1e
--- /dev/null
+++ b/tests/smoke/plain-filename-autolink.spec.ts
@@ -0,0 +1,108 @@
+import { expect, test, type Page } from '@playwright/test'
+import {
+  createFixtureVaultCopy,
+  openFixtureVault,
+  removeFixtureVaultCopy,
+} from '../helpers/fixtureVault'
+import { executeCommand, openCommandPalette } from './helpers'
+
+let tempVaultDir: string
+
+async function openNote(page: Page, title: string) {
+  await page.locator('[data-testid="note-list-container"]').getByText(title, { exact: true }).click()
+  await expect(page.locator('.bn-editor')).toBeVisible({ timeout: 5_000 })
+}
+
+async function openRawMode(page: Page) {
+  await openCommandPalette(page)
+  await executeCommand(page, 'Toggle Raw')
+  await expect(page.locator('.cm-content')).toBeVisible({ timeout: 5_000 })
+}
+
+async function openBlockNoteMode(page: Page) {
+  await openCommandPalette(page)
+  await executeCommand(page, 'Toggle Raw')
+  await expect(page.locator('.bn-editor')).toBeVisible({ timeout: 5_000 })
+}
+
+async function getRawEditorContent(page: Page): Promise<string> {
+  return page.evaluate(() => {
+    const el = document.querySelector('.cm-content')
+    if (!el) return ''
+
+    // eslint-disable-next-line @typescript-eslint/no-explicit-any -- CodeMirror view is attached to the DOM node.
+    const view = (el as any).cmTile?.view
+    if (!view) return el.textContent ?? ''
+
+    return view.state.doc.toString() as string
+  })
+}
+
+async function setRawEditorContent(page: Page, content: string) {
+  await page.evaluate((nextContent) => {
+    const el = document.querySelector('.cm-content')
+    if (!el) return
+
+    // eslint-disable-next-line @typescript-eslint/no-explicit-any -- CodeMirror view is attached to the DOM node.
+    const view = (el as any).cmTile?.view
+    if (!view) return
+
+    view.dispatch({
+      changes: {
+        from: 0,
+        to: view.state.doc.length,
+        insert: nextContent,
+      },
+    })
+  }, content)
+}
+
+async function appendPlainFilenameParagraph(page: Page, value: string) {
+  const lastBlock = page.locator('.bn-block-content').last()
+  await expect(lastBlock).toBeVisible({ timeout: 5_000 })
+  await lastBlock.click()
+  await page.keyboard.press('End')
+  await page.keyboard.press('Enter')
+  await page.keyboard.type(`${value} `)
+  await page.waitForTimeout(700)
+}
+
+test.beforeEach(async ({ page }, testInfo) => {
+  testInfo.setTimeout(90_000)
+  tempVaultDir = createFixtureVaultCopy()
+  await openFixtureVault(page, tempVaultDir)
+})
+
+test.afterEach(async () => {
+  removeFixtureVaultCopy(tempVaultDir)
+})
+
+test('plain filename-like text typed in BlockNote stays plain through raw-mode round trips', async ({ page }) => {
+  await openNote(page, 'Note B')
+  await appendPlainFilenameParagraph(page, 'AGENTS.md')
+  await appendPlainFilenameParagraph(page, 'docs/README.md')
+
+  await openRawMode(page)
+
+  const raw = await getRawEditorContent(page)
+  expect(raw).toContain('AGENTS.md')
+  expect(raw).toContain('docs/README.md')
+  expect(raw).not.toMatch(/\[AGENTS\.md\]\(/)
+  expect(raw).not.toMatch(/\[docs\/README\.md\]\(/)
+})
+
+test('explicit markdown links still render and round-trip intentionally', async ({ page }) => {
+  await openNote(page, 'Note B')
+  await openRawMode(page)
+
+  const raw = await getRawEditorContent(page)
+  const intentionalLink = '[Tolaria Docs](https://example.com/docs)'
+  await setRawEditorContent(page, `${raw}\n\n${intentionalLink}\n`)
+  await page.waitForTimeout(700)
+
+  await openBlockNoteMode(page)
+  await expect(page.locator('.bn-editor a[href="https://example.com/docs"]').last()).toContainText('Tolaria Docs')
+
+  await openRawMode(page)
+  await expect.poll(() => getRawEditorContent(page)).toContain(intentionalLink)
+})