diff --git a/apps/desktop/src/app/chat/composer/index.tsx b/apps/desktop/src/app/chat/composer/index.tsx
index 1ce110f4e098..a29dcb1cd7e3 100644
--- a/apps/desktop/src/app/chat/composer/index.tsx
+++ b/apps/desktop/src/app/chat/composer/index.tsx
@@ -49,7 +49,7 @@ import {
   composerPlainText,
   deleteChipBeforeCaret,
   deleteSelectionInEditor,
-  insertPlainTextAtCaret,
+  insertComposerContentsAtCaret,
   normalizeComposerEditorDom,
   RICH_INPUT_SLOT
 } from './rich-editor'
@@ -60,6 +60,7 @@ import { extractClipboardImageBlobs } from './text-utils'
 import { ComposerTriggerPopover } from './trigger-popover'
 import type { ChatBarProps } from './types'
 import { UrlDialog } from './url-dialog'
+import { chipTypedUrlOnSpace, linkifyUrls } from './url-refs'
 import { VoiceActivity, VoicePlaybackActivity } from './voice-activity'
 
 export function ChatBar({
@@ -402,7 +403,11 @@ export function ChatBar({
     }
 
     event.preventDefault()
-    insertPlainTextAtCaret(event.currentTarget, pastedText)
+
+    // Links in the paste land as `@url:` chips rather than a wall of URL text —
+    // the same reference the "Add URL" dialog inserts, parsed in place so a link
+    // mid-sentence keeps its position.
+    insertComposerContentsAtCaret(event.currentTarget, linkifyUrls(pastedText))
     scheduleFlushEditorToDraft(event.currentTarget)
   }
 
@@ -441,6 +446,15 @@ export function ChatBar({
       return
     }
 
+    // A typed link finished with a space chips like a pasted one — the space
+    // itself rides along inside the insert.
+    if (chipTypedUrlOnSpace(event)) {
+      event.preventDefault()
+      flushEditorToDraft(event.currentTarget)
+
+      return
+    }
+
     // Cmd/Ctrl+Shift+K drains the next queued message. Plain Cmd/Ctrl+K is
     // reserved for the global command palette.
     if ((event.metaKey || event.ctrlKey) && !event.altKey && event.shiftKey && event.key.toLowerCase() === 'k') {
diff --git a/apps/desktop/src/app/chat/composer/rich-editor.test.ts b/apps/desktop/src/app/chat/composer/rich-editor.test.ts
index 12e3e9613eff..aa4e80aedb9c 100644
--- a/apps/desktop/src/app/chat/composer/rich-editor.test.ts
+++ b/apps/desktop/src/app/chat/composer/rich-editor.test.ts
@@ -4,10 +4,11 @@ import { insertInlineRefsIntoEditor } from './inline-refs'
 import {
   composerPlainText,
   deleteSelectionInEditor,
-  insertPlainTextAtCaret,
+  insertComposerContentsAtCaret,
   normalizeComposerEditorDom,
   refChipElement,
   renderComposerContents,
+  replaceBeforeCaret,
   RICH_INPUT_SLOT
 } from './rich-editor'
 
@@ -72,14 +73,14 @@ describe('insertInlineRefsIntoEditor', () => {
   })
 })
 
-describe('insertPlainTextAtCaret', () => {
+describe('insertComposerContentsAtCaret', () => {
   it('inserts multiline text as text nodes + br', () => {
     const editor = document.createElement('div')
     editor.dataset.slot = RICH_INPUT_SLOT
     document.body.append(editor)
     caretIn(editor)
 
-    insertPlainTextAtCaret(editor, 'one\ntwo\nthree')
+    insertComposerContentsAtCaret(editor, 'one\ntwo\nthree')
 
     expect(editor.querySelectorAll('br').length).toBe(2)
     expect(composerPlainText(editor)).toBe('one\ntwo\nthree')
@@ -102,12 +103,76 @@ describe('insertPlainTextAtCaret', () => {
     selection.removeAllRanges()
     selection.addRange(range)
 
-    insertPlainTextAtCaret(editor, 'cd')
+    insertComposerContentsAtCaret(editor, 'cd')
 
     expect(composerPlainText(editor)).toBe('abcdef')
 
     editor.remove()
   })
+
+  it('lands directives in the text as chips', () => {
+    const editor = document.createElement('div')
+    editor.dataset.slot = RICH_INPUT_SLOT
+    document.body.append(editor)
+    caretIn(editor)
+
+    insertComposerContentsAtCaret(editor, 'read @url:`https://example.dev/a` now')
+
+    expect(editor.querySelectorAll('[data-ref-kind="url"]').length).toBe(1)
+    expect(composerPlainText(editor)).toBe('read @url:`https://example.dev/a` now')
+
+    editor.remove()
+  })
+})
+
+describe('replaceBeforeCaret', () => {
+  it('swaps the token before the caret and leaves the caret after the insert', () => {
+    const editor = document.createElement('div')
+    editor.dataset.slot = RICH_INPUT_SLOT
+    editor.textContent = 'see foo'
+    document.body.append(editor)
+
+    const text = editor.firstChild!
+    const selection = window.getSelection()!
+    const range = document.createRange()
+
+    range.setStart(text, 7)
+    range.collapse(true)
+    selection.removeAllRanges()
+    selection.addRange(range)
+
+    const fragment = document.createDocumentFragment()
+    fragment.append(refChipElement('file', '`src/foo.ts`'), document.createTextNode(' '))
+
+    expect(replaceBeforeCaret(editor, 3, fragment)).toBe(true)
+    expect(composerPlainText(editor)).toBe('see @file:`src/foo.ts` ')
+    expect(selection.getRangeAt(0).collapsed).toBe(true)
+
+    editor.remove()
+  })
+
+  it('leaves the editor alone when the caret has no room for the token', () => {
+    const editor = document.createElement('div')
+    editor.dataset.slot = RICH_INPUT_SLOT
+    editor.textContent = 'hi'
+    document.body.append(editor)
+
+    const selection = window.getSelection()!
+    const range = document.createRange()
+
+    range.setStart(editor.firstChild!, 2)
+    range.collapse(true)
+    selection.removeAllRanges()
+    selection.addRange(range)
+
+    const fragment = document.createDocumentFragment()
+    fragment.append(document.createTextNode('x'))
+
+    expect(replaceBeforeCaret(editor, 20, fragment)).toBe(false)
+    expect(composerPlainText(editor)).toBe('hi')
+
+    editor.remove()
+  })
 })
 
 describe('deleteSelectionInEditor', () => {
diff --git a/apps/desktop/src/app/chat/composer/rich-editor.ts b/apps/desktop/src/app/chat/composer/rich-editor.ts
index 21f0286c9f82..738201fc3944 100644
--- a/apps/desktop/src/app/chat/composer/rich-editor.ts
+++ b/apps/desktop/src/app/chat/composer/rich-editor.ts
@@ -11,11 +11,11 @@ import {
   directiveIconElement,
   directiveIconSvg,
   formatRefValue,
+  refChipLabel,
   slashChipClass,
   type SlashChipKind,
   slashIconElement
 } from '@/components/assistant-ui/directive-text'
-import { sessionRefFallbackLabel } from '@/lib/session-refs'
 
 export const RICH_INPUT_SLOT = 'composer-rich-input'
 
@@ -35,10 +35,6 @@ export function unquoteRef(raw: string) {
   return quoted ? raw.slice(1, -1) : raw.replace(/[,.;!?]+$/, '')
 }
 
-export function refLabel(id: string) {
-  return id.split(/[\\/]/).filter(Boolean).pop() || id
-}
-
 /** Always-quote variant of formatRefValue — chips need a fence even for safe values. */
 export function quoteRefValue(value: string) {
   if (!value.includes('`')) {
@@ -60,9 +56,9 @@ export function refChipHtml(kind: string, rawValue: string, displayLabel?: strin
   const id = unquoteRef(rawValue)
   const text = `@${kind}:${quoteRefValue(id)}`
 
-  const label = displayLabel || (kind === 'session' ? sessionRefFallbackLabel(id) : refLabel(id))
+  const label = displayLabel || refChipLabel(kind, id)
 
-  return `<span contenteditable="false" data-ref-text="${escapeHtml(text)}" data-ref-id="${escapeHtml(id)}" data-ref-kind="${escapeHtml(kind)}" class="${DIRECTIVE_CHIP_CLASS}">${directiveIconSvg(kind)}<span class="truncate">${escapeHtml(label)}</span></span>`
+  return `<span contenteditable="false" title="${escapeHtml(id)}" data-ref-text="${escapeHtml(text)}" data-ref-id="${escapeHtml(id)}" data-ref-kind="${escapeHtml(kind)}" class="${DIRECTIVE_CHIP_CLASS}">${directiveIconSvg(kind)}<span class="truncate">${escapeHtml(label)}</span></span>`
 }
 
 export function refChipElement(kind: string, rawValue: string, displayLabel?: string) {
@@ -72,12 +68,13 @@ export function refChipElement(kind: string, rawValue: string, displayLabel?: st
   const label = document.createElement('span')
 
   chip.contentEditable = 'false'
+  chip.title = id
   chip.dataset.refText = text
   chip.dataset.refId = id
   chip.dataset.refKind = kind
   chip.className = DIRECTIVE_CHIP_CLASS
   label.className = 'truncate'
-  label.textContent = displayLabel || (kind === 'session' ? sessionRefFallbackLabel(id) : refLabel(id))
+  label.textContent = displayLabel || refChipLabel(kind, id)
   chip.append(directiveIconElement(kind), label)
 
   return chip
@@ -147,14 +144,15 @@ function composerSelectionRange(editor: HTMLElement) {
   return { range, selection }
 }
 
-/** Insert plain text at the caret (replacing any selection). Pastes use this
- *  instead of `execCommand('insertText')` — Chromium's editing pipeline is
- *  ~O(n²) on large multiline blobs. */
-export function insertPlainTextAtCaret(editor: HTMLElement, text: string) {
+/** Insert text at the caret (replacing any selection), with any `@kind:value`
+ *  directives in it landing as chips. Pastes use this instead of
+ *  `execCommand('insertText')` — Chromium's editing pipeline is ~O(n²) on large
+ *  multiline blobs. */
+export function insertComposerContentsAtCaret(editor: HTMLElement, text: string) {
   const hit = composerSelectionRange(editor)
   const fragment = document.createDocumentFragment()
 
-  appendTextWithBreaks(fragment, text)
+  appendComposerContents(fragment, text)
 
   const tail = fragment.lastChild
 
@@ -175,6 +173,41 @@ export function insertPlainTextAtCaret(editor: HTMLElement, text: string) {
   }
 }
 
+/** Swap the `length` characters immediately before a collapsed caret for
+ *  `fragment`, leaving the caret after it. Returns whether it ran — a caret that
+ *  isn't inside a text node holding the whole token is left alone. */
+export function replaceBeforeCaret(editor: HTMLElement, length: number, fragment: DocumentFragment) {
+  const hit = composerSelectionRange(editor)
+
+  if (!hit?.range.collapsed) {
+    return false
+  }
+
+  const { startContainer, startOffset } = hit.range
+
+  if (startContainer.nodeType !== Node.TEXT_NODE || startOffset < length) {
+    return false
+  }
+
+  const range = document.createRange()
+  const tail = fragment.lastChild
+
+  range.setStart(startContainer, startOffset - length)
+  range.setEnd(startContainer, startOffset)
+  range.deleteContents()
+  range.insertNode(fragment)
+
+  if (tail) {
+    range.setStartAfter(tail)
+  }
+
+  range.collapse(true)
+  hit.selection.removeAllRanges()
+  hit.selection.addRange(range)
+
+  return true
+}
+
 /** Backspace at a collapsed caret immediately after a chip: delete the chip AND
  *  the single trailing space we auto-insert after it, atomically — so removing a
  *  directive never strands an orphaned space (the contenteditable-driven cleanup
diff --git a/apps/desktop/src/app/chat/composer/url-refs.test.ts b/apps/desktop/src/app/chat/composer/url-refs.test.ts
new file mode 100644
index 000000000000..febbd533ce43
--- /dev/null
+++ b/apps/desktop/src/app/chat/composer/url-refs.test.ts
@@ -0,0 +1,98 @@
+import type { KeyboardEvent } from 'react'
+import { describe, expect, it } from 'vitest'
+
+import { composerPlainText, RICH_INPUT_SLOT } from './rich-editor'
+import { chipTypedUrlOnSpace, linkifyUrls } from './url-refs'
+
+/** An editor holding `text` with a collapsed caret at `caret`, plus the space
+ *  keydown the composer would hand `chipTypedUrlOnSpace`. */
+const spaceOn = (text: string, caret: number) => {
+  const editor = document.createElement('div')
+  editor.dataset.slot = RICH_INPUT_SLOT
+  editor.textContent = text
+  document.body.append(editor)
+
+  const selection = window.getSelection()!
+  const range = document.createRange()
+
+  range.setStart(editor.firstChild!, caret)
+  range.collapse(true)
+  selection.removeAllRanges()
+  selection.addRange(range)
+
+  return { editor, event: { currentTarget: editor, key: ' ' } as KeyboardEvent<HTMLDivElement> }
+}
+
+describe('linkifyUrls', () => {
+  it('rewrites a bare link as a url directive', () => {
+    expect(linkifyUrls('https://example.dev/a/b')).toBe('@url:`https://example.dev/a/b`')
+  })
+
+  it('keeps the link in place mid-sentence and leaves its punctuation behind', () => {
+    expect(linkifyUrls('read https://example.dev/a. then stop')).toBe('read @url:`https://example.dev/a`. then stop')
+  })
+
+  it('keeps balanced parens but drops the one that closed the sentence', () => {
+    expect(linkifyUrls('(see https://en.wikipedia.org/wiki/A_(b))')).toBe(
+      '(see @url:`https://en.wikipedia.org/wiki/A_(b)`)'
+    )
+  })
+
+  it('rewrites every link in a multi-link paste', () => {
+    expect(linkifyUrls('http://a.dev and https://b.dev')).toBe('@url:`http://a.dev` and @url:`https://b.dev`')
+  })
+
+  it('leaves a link that is already a directive alone', () => {
+    expect(linkifyUrls('@url:`https://example.dev`')).toBe('@url:`https://example.dev`')
+  })
+
+  it('leaves text without a scheme alone', () => {
+    expect(linkifyUrls('example.dev/a and src/foo.ts')).toBe('example.dev/a and src/foo.ts')
+  })
+})
+
+describe('chipTypedUrlOnSpace', () => {
+  it('chips a link typed right before the caret and adds the space', () => {
+    const { editor, event } = spaceOn('see https://example.dev/a', 25)
+
+    expect(chipTypedUrlOnSpace(event)).toBe(true)
+    expect(composerPlainText(editor)).toBe('see @url:`https://example.dev/a` ')
+
+    editor.remove()
+  })
+
+  it('keeps sentence punctuation outside the chip', () => {
+    const { editor, event } = spaceOn('https://example.dev.', 20)
+
+    expect(chipTypedUrlOnSpace(event)).toBe(true)
+    expect(composerPlainText(editor)).toBe('@url:`https://example.dev`. ')
+
+    editor.remove()
+  })
+
+  it('ignores a caret that is not sitting on a link', () => {
+    const { editor, event } = spaceOn('https://example.dev is nice', 27)
+
+    expect(chipTypedUrlOnSpace(event)).toBe(false)
+    expect(composerPlainText(editor)).toBe('https://example.dev is nice')
+
+    editor.remove()
+  })
+
+  it('ignores a scheme with no host yet', () => {
+    const { editor, event } = spaceOn('https://', 8)
+
+    expect(chipTypedUrlOnSpace(event)).toBe(false)
+
+    editor.remove()
+  })
+
+  it('leaves a modified space alone', () => {
+    const { editor, event } = spaceOn('https://example.dev', 19)
+
+    expect(chipTypedUrlOnSpace({ ...event, altKey: true })).toBe(false)
+    expect(composerPlainText(editor)).toBe('https://example.dev')
+
+    editor.remove()
+  })
+})
diff --git a/apps/desktop/src/app/chat/composer/url-refs.ts b/apps/desktop/src/app/chat/composer/url-refs.ts
new file mode 100644
index 000000000000..580abdc1c6fb
--- /dev/null
+++ b/apps/desktop/src/app/chat/composer/url-refs.ts
@@ -0,0 +1,103 @@
+/**
+ * Bare-link recognition for the composer. A link the user pastes or types is the
+ * same thing the "+ → Add URL" dialog inserts, so it becomes an `@url:`
+ * directive: a chip that truncates instead of a wall of URL text, and a
+ * reference the gateway resolves.
+ */
+import type { KeyboardEvent } from 'react'
+
+import { quoteRefValue, REF_RE, refChipElement, replaceBeforeCaret } from './rich-editor'
+import { textBeforeCaret } from './text-utils'
+
+// An explicit scheme only — `example.com` bare is too easy to hit by accident
+// (a filename, a version, a sentence). Brackets and quotes fence a URL in prose;
+// parens don't, so they stay in and an unbalanced tail is trimmed below.
+const URL_RE = /https?:\/\/[^\s<>[\]{}"'`]+/gi
+const TYPED_URL_RE = /(?:^|\s)(https?:\/\/[^\s<>[\]{}"'`]+)$/i
+
+/** A URL at the end of a sentence carries the punctuation that ended it. */
+function splitUrlTail(raw: string) {
+  let url = raw.replace(/[,.;:!?]+$/, '')
+
+  while (url.endsWith(')') && url.split(')').length > url.split('(').length) {
+    url = url.slice(0, -1)
+  }
+
+  return { trailing: raw.slice(url.length), url }
+}
+
+/** A URL needs a host past the scheme to be worth chipping. */
+const hasHost = (url: string) => /^https?:\/\/[^/\s]/i.test(url)
+
+/** Rewrite bare links in `text` as `@url:` directives, leaving links that are
+ *  already part of a directive alone. Returns `text` unchanged when there are
+ *  none. */
+export function linkifyUrls(text: string) {
+  REF_RE.lastIndex = 0
+
+  const fenced = Array.from(text.matchAll(REF_RE)).map(match => {
+    const start = match.index ?? 0
+
+    return { end: start + match[0].length, start }
+  })
+
+  let out = ''
+  let cursor = 0
+
+  for (const match of text.matchAll(URL_RE)) {
+    const start = match.index ?? 0
+    const { url } = splitUrlTail(match[0])
+
+    if (!hasHost(url) || fenced.some(span => start >= span.start && start < span.end)) {
+      continue
+    }
+
+    out += `${text.slice(cursor, start)}@url:${quoteRefValue(url)}`
+    cursor = start + url.length
+  }
+
+  return out + text.slice(cursor)
+}
+
+/** A plain space finishing a typed link commits it as a chip (followed by
+ *  whatever punctuation ended it, then the space). Returns whether it ran, so a
+ *  keydown handler can fall through on anything else. */
+export function chipTypedUrlOnSpace(event: KeyboardEvent<HTMLDivElement>) {
+  if (event.key !== ' ' || event.metaKey || event.ctrlKey || event.altKey) {
+    return false
+  }
+
+  const editor = event.currentTarget
+
+  // Runs on every space, so bail on the cheap native read before paying for the
+  // caret range walk (same guard shape as the trigger detector).
+  if (!editor.textContent?.includes('://')) {
+    return false
+  }
+
+  const before = textBeforeCaret(editor)
+  const match = before ? TYPED_URL_RE.exec(before) : null
+  const token = match?.[1]
+
+  if (!token) {
+    return false
+  }
+
+  const { trailing, url } = splitUrlTail(token)
+
+  if (!hasHost(url)) {
+    return false
+  }
+
+  const fragment = document.createDocumentFragment()
+
+  fragment.append(refChipElement('url', quoteRefValue(url)))
+
+  if (trailing) {
+    fragment.append(document.createTextNode(trailing))
+  }
+
+  fragment.append(document.createTextNode(' '))
+
+  return replaceBeforeCaret(editor, token.length, fragment)
+}
diff --git a/apps/desktop/src/components/assistant-ui/directive-text.tsx b/apps/desktop/src/components/assistant-ui/directive-text.tsx
index 317489a96f82..312c7d9414d8 100644
--- a/apps/desktop/src/components/assistant-ui/directive-text.tsx
+++ b/apps/desktop/src/components/assistant-ui/directive-text.tsx
@@ -277,7 +277,7 @@ function parseDirectiveText(text: string): Unstable_DirectiveSegment[] {
         start: match.index ?? 0,
         end: (match.index ?? 0) + match[0].length,
         type: match[1] || 'file',
-        label: shortLabel(match[1] as HermesRefType, id),
+        label: refChipLabel(match[1] || 'file', id),
         id
       }
     }),
@@ -320,25 +320,30 @@ function parseDirectiveText(text: string): Unstable_DirectiveSegment[] {
   return segments
 }
 
-function shortLabel(type: HermesRefType, id: string): string {
+/** Display text for a `@kind:value` chip. Shared with the composer's
+ *  contenteditable chips so a link reads the same before and after send: the
+ *  host leads (scheme and `www.` are noise) and the path rides along for the
+ *  chip's `truncate` to cut — a bare hostname can't tell two links apart. */
+export function refChipLabel(type: string, id: string): string {
   if (type === 'terminal') {
     return id || 'terminal'
   }
 
+  if (type === 'session') {
+    return sessionRefFallbackLabel(id)
+  }
+
   if (type === 'url') {
     try {
-      const parsed = new URL(id)
+      const { hostname, pathname, search } = new URL(id)
+      const path = `${pathname}${search}`.replace(/\/$/, '')
 
-      return parsed.hostname || id
+      return `${hostname.replace(/^www\./i, '')}${path}` || id
     } catch {
       return id
     }
   }
 
-  if (type === 'session') {
-    return sessionRefFallbackLabel(id)
-  }
-
   const tail = id.split(/[\\/]/).filter(Boolean).pop()
 
   return tail || id
diff --git a/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx b/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx
index b29e13493ef5..0da6e1dea8a8 100644
--- a/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx
+++ b/apps/desktop/src/components/assistant-ui/thread/user-edit-composer.tsx
@@ -31,6 +31,7 @@ import {
 } from '@/app/chat/composer/inline-refs'
 import {
   composerPlainText,
+  insertComposerContentsAtCaret,
   placeCaretEnd,
   refChipElement,
   renderComposerContents,
@@ -38,6 +39,7 @@ import {
 } from '@/app/chat/composer/rich-editor'
 import { detectTrigger, textBeforeCaret, type TriggerState } from '@/app/chat/composer/text-utils'
 import { ComposerTriggerPopover } from '@/app/chat/composer/trigger-popover'
+import { chipTypedUrlOnSpace, linkifyUrls } from '@/app/chat/composer/url-refs'
 import {
   extractDroppedFiles,
   HERMES_PATHS_MIME,
@@ -503,7 +505,9 @@ export const UserEditComposer: FC<UserEditComposerProps> = ({ cwd, gateway, sess
 
     event.preventDefault()
     rememberInitialDraft()
-    document.execCommand('insertText', false, pastedText)
+
+    // Links land as `@url:` chips, same as the main composer.
+    insertComposerContentsAtCaret(event.currentTarget, linkifyUrls(pastedText))
     syncDraftFromEditor(event.currentTarget)
   }
 
@@ -602,6 +606,15 @@ export const UserEditComposer: FC<UserEditComposerProps> = ({ cwd, gateway, sess
       return
     }
 
+    // A typed link finished with a space chips like a pasted one.
+    if (chipTypedUrlOnSpace(event)) {
+      event.preventDefault()
+      rememberInitialDraft()
+      syncDraftFromEditor(event.currentTarget)
+
+      return
+    }
+
     if (event.key === 'Enter' && !event.shiftKey) {
       event.preventDefault()
       submitEdit(event.currentTarget)