diff --git a/web/components/bio/editable-bio.tsx b/web/components/bio/editable-bio.tsx
index c278e5c8..a3287687 100644
--- a/web/components/bio/editable-bio.tsx
+++ b/web/components/bio/editable-bio.tsx
@@ -9,7 +9,7 @@ import {useRouter} from 'next/router'
 import {useEffect, useState} from 'react'
 import ReactMarkdown from 'react-markdown'
 import {Button} from 'web/components/buttons/button'
-import {linkifyTrailingUrl} from 'web/components/editor/autolink'
+import {linkifyUrls} from 'web/components/editor/autolink'
 import {Col} from 'web/components/layout/col'
 import {Row} from 'web/components/layout/row'
 import {TextEditor, useTextEditor} from 'web/components/widgets/editor'
@@ -77,7 +77,7 @@ export function EditableBio(props: {profile: Profile; onSave: () => void; onCanc
 
   const saveBio = async () => {
     if (!editor) return
-    linkifyTrailingUrl(editor)
+    linkifyUrls(editor)
     // console.log(editor.getText().length)
     const {error} = await tryCatch(
       updateProfile({
diff --git a/web/components/comments/comment-input.tsx b/web/components/comments/comment-input.tsx
index e58cd26c..9ce48056 100644
--- a/web/components/comments/comment-input.tsx
+++ b/web/components/comments/comment-input.tsx
@@ -14,7 +14,7 @@ import {useT} from 'web/lib/locale'
 import {track} from 'web/lib/service/analytics'
 import {safeLocalStorage} from 'web/lib/util/local'
 
-import {linkifyTrailingUrl} from '../editor/autolink'
+import {linkifyUrls} from '../editor/autolink'
 import {Row} from '../layout/row'
 import {Avatar} from '../widgets/avatar'
 import {TextEditor, useTextEditor} from '../widgets/editor'
@@ -156,7 +156,7 @@ export function CommentInputTextArea(props: {
   // through this, so a message ending in a URL gets that URL linked whichever one you used. TipTap's
   // autolink can't do it itself: it only fires once you type a separator *after* the URL.
   const submitWithTrailingLink = useEvent((type: CommentType) => {
-    if (editor) linkifyTrailingUrl(editor)
+    if (editor) linkifyUrls(editor)
     submit?.(type)
   })
 
diff --git a/web/components/contact.tsx b/web/components/contact.tsx
index 9e784774..25430b62 100644
--- a/web/components/contact.tsx
+++ b/web/components/contact.tsx
@@ -5,7 +5,7 @@ import {MAX_DESCRIPTION_LENGTH} from 'common/envs/constants'
 import Link from 'next/link'
 import toast from 'react-hot-toast'
 import {Button} from 'web/components/buttons/button'
-import {linkifyTrailingUrl} from 'web/components/editor/autolink'
+import {linkifyUrls} from 'web/components/editor/autolink'
 import {Col} from 'web/components/layout/col'
 import {Row} from 'web/components/layout/row'
 import {TextEditor, useTextEditor} from 'web/components/widgets/editor'
@@ -55,7 +55,7 @@ export function ContactComponent() {
               size="xs"
               onClick={async () => {
                 if (!editor) return
-                linkifyTrailingUrl(editor)
+                linkifyUrls(editor)
                 const data = {
                   content: editor.getJSON() as JSONContent,
                   userId: user?.id,
diff --git a/web/components/editor/autolink.ts b/web/components/editor/autolink.ts
index 96965226..0b239f12 100644
--- a/web/components/editor/autolink.ts
+++ b/web/components/editor/autolink.ts
@@ -6,7 +6,7 @@ import {
   getMarkRange,
 } from '@tiptap/core'
 import type {Mark, MarkType, Node as PMNode} from '@tiptap/pm/model'
-import {Plugin, PluginKey} from '@tiptap/pm/state'
+import {Plugin, PluginKey, type Transaction} from '@tiptap/pm/state'
 import {tokenize} from 'linkifyjs'
 
 /** Protocol assumed for bare hosts like `example.com`. Matches what `Link` is configured with. */
@@ -26,42 +26,57 @@ const hrefOf = (text: string) => {
 }
 
 /**
- * Link a URL sitting at the very end of the doc.
+ * Add link marks to every bare URL in the doc that doesn't have one yet, writing into `tr`.
  *
- * TipTap's autolink only fires once a separator is typed *after* a URL (a space, or the enter that
- * splits the block), so a message whose last word is a URL is submitted as plain text. Call this
- * right before reading the content out of the editor — same rules as the autolink plugin, so the
- * result is identical to what you'd get by typing a trailing space.
+ * Returns whether anything was marked. Shared by the on-send pass and the on-paste plugin so both
+ * agree, to the character, on what counts as a URL.
  */
-export const linkifyTrailingUrl = (editor: Editor) => {
-  const linkType = editor.state.schema.marks.link
-  if (!linkType) return
+const addLinkMarks = (doc: PMNode, tr: Transaction, linkType: MarkType, codeType?: MarkType) => {
+  let changed = false
 
-  const {doc} = editor.state
-  let block: {node: PMNode; pos: number} | undefined
   doc.descendants((node, pos) => {
-    if (!node.isTextblock) return true
-    block = {node, pos}
+    if (!node.isTextblock) return true // a list item / table cell / blockquote: keep descending
+    if (node.type.spec.code) return false // a code block is literal text, not prose
+
+    // The block's first content position, one past the block node itself. Leaf nodes (hard breaks,
+    // mentions, emoji) are read as a single space, which is both what the autolink plugin does and
+    // what keeps string offsets lined up one-to-one with document positions.
+    const start = pos + 1
+    const text = doc.textBetween(start, pos + node.nodeSize - 1, undefined, ' ')
+
+    tokenize(text).forEach((token) => {
+      if (!token.isLink) return
+      const from = start + token.startIndex()
+      const to = start + token.endIndex()
+      if (doc.rangeHasMark(from, to, linkType)) return // already linked, by hand or by autolink
+      if (codeType && doc.rangeHasMark(from, to, codeType)) return
+      tr.addMark(from, to, linkType.create({href: token.toObject(DEFAULT_PROTOCOL).href}))
+      changed = true
+    })
+
     return false // no textblocks nested inside a textblock
   })
-  if (!block) return
 
-  // Hard breaks count as spaces, matching how the autolink plugin reads a block.
-  const text = doc.textBetween(block.pos, block.pos + block.node.nodeSize, undefined, ' ')
-  const lastWord = text.split(' ').filter(Boolean).pop()
-  if (!lastWord || !text.endsWith(lastWord)) return // trailing space: autolink already had its turn
+  return changed
+}
 
-  const href = hrefOf(lastWord)
-  if (!href) return
+/**
+ * Link every bare URL in the doc, including protocol-less ones like `compassmeet.com/heartborne`.
+ *
+ * TipTap's autolink only fires on the keystroke *after* a URL (a space, or the enter that splits the
+ * block), so a message whose last word is a URL is submitted as plain text — and text arriving any
+ * way other than typing (paste, programmatic insert) is never seen by it at all. Call this right
+ * before reading the content out of the editor; it uses the same rules as the autolink plugin, so
+ * the result is what you'd have got by typing every URL and following it with a space.
+ */
+export const linkifyUrls = (editor: Editor) => {
+  const {schema, tr, doc} = editor.state
+  const linkType = schema.marks.link
+  if (!linkType) return
 
-  // `text` starts at the block's first content position, one past the block node itself.
-  const from = block.pos + text.lastIndexOf(lastWord) + 1
-  const to = from + lastWord.length
-  const {code} = editor.state.schema.marks
-  if (doc.rangeHasMark(from, to, linkType)) return
-  if (code && doc.rangeHasMark(from, to, code)) return
-
-  editor.view.dispatch(editor.state.tr.addMark(from, to, linkType.create({href})))
+  if (addLinkMarks(doc, tr, linkType, schema.marks.code)) {
+    editor.view.dispatch(tr.setMeta('preventAutolink', true))
+  }
 }
 
 /** Every distinct link-marked run of text overlapping [from, to], each expanded to its full extent. */
@@ -152,6 +167,34 @@ export const SyncAutolink = Extension.create({
           return tr.steps.length ? tr : undefined
         },
       }),
+
+      /**
+       * Linkify pasted URLs.
+       *
+       * TipTap's own paste handling only links a URL pasted *over a selection*; a plain paste is left
+       * to the autolink plugin, which never sees it because it only reacts to typed separators. So
+       * pasting a list of links yields a list of plain text. Re-scanning the whole doc after a paste
+       * is cheap at the sizes this editor holds (a message, a bio) and, unlike scanning the pasted
+       * slice, it also catches a URL completed by the paste landing next to existing text.
+       */
+      new Plugin({
+        key: new PluginKey('linkifyOnPaste'),
+        appendTransaction: (transactions, _oldState, newState) => {
+          const pasted = transactions.some(
+            (transaction) =>
+              transaction.docChanged &&
+              (transaction.getMeta('paste') || transaction.getMeta('uiEvent') === 'drop'),
+          )
+          const prevented = transactions.some((transaction) =>
+            transaction.getMeta('preventAutolink'),
+          )
+          if (!pasted || prevented) return
+
+          const {tr} = newState
+          const {code} = newState.schema.marks
+          return addLinkMarks(newState.doc, tr, linkType, code) ? tr : undefined
+        },
+      }),
     ]
   },
 })
diff --git a/web/components/messaging/send-message-button.tsx b/web/components/messaging/send-message-button.tsx
index 2cc81867..1c85ff15 100644
--- a/web/components/messaging/send-message-button.tsx
+++ b/web/components/messaging/send-message-button.tsx
@@ -10,7 +10,7 @@ import React, {useEffect, useRef, useState} from 'react'
 import {BiEnvelope} from 'react-icons/bi'
 import {Button, buttonClass} from 'web/components/buttons/button'
 import {CommentInputTextArea} from 'web/components/comments/comment-input'
-import {linkifyTrailingUrl} from 'web/components/editor/autolink'
+import {linkifyUrls} from 'web/components/editor/autolink'
 import {Col} from 'web/components/layout/col'
 import {Modal, MODAL_CLASS} from 'web/components/layout/modal'
 import {Row} from 'web/components/layout/row'
@@ -146,7 +146,7 @@ export const SendMessageButton = (props: {
     })
     if (!res) return
 
-    linkifyTrailingUrl(editor)
+    linkifyUrls(editor)
     const msgRes = await api('create-private-user-message', {
       channelId: res.channelId,
       content: editor.getJSON(),
diff --git a/web/components/votes/vote-info.tsx b/web/components/votes/vote-info.tsx
index 4f95d61d..3e1acee7 100644
--- a/web/components/votes/vote-info.tsx
+++ b/web/components/votes/vote-info.tsx
@@ -9,7 +9,7 @@ import Link from 'next/link'
 import {useEffect, useMemo, useState} from 'react'
 import toast from 'react-hot-toast'
 import {Button} from 'web/components/buttons/button'
-import {linkifyTrailingUrl} from 'web/components/editor/autolink'
+import {linkifyUrls} from 'web/components/editor/autolink'
 import {Col} from 'web/components/layout/col'
 import {Row} from 'web/components/layout/row'
 import {EnglishOnlyWarning} from 'web/components/news/english-only-warning'
@@ -167,7 +167,7 @@ export function VoteComponent() {
                     size="sm"
                     color="cta"
                     onClick={async () => {
-                      linkifyTrailingUrl(editor)
+                      linkifyUrls(editor)
                       const data = {
                         title: title,
                         description: editor.getJSON() as JSONContent,
diff --git a/web/components/widgets/editor.tsx b/web/components/widgets/editor.tsx
index ebfa3397..85a4fab9 100644
--- a/web/components/widgets/editor.tsx
+++ b/web/components/widgets/editor.tsx
@@ -20,7 +20,7 @@ import {MediaModal} from 'web/components/media-modal'
 import {usePersistentLocalState} from 'web/hooks/use-persistent-local-state'
 import {safeLocalStorage} from 'web/lib/util/local'
 
-import {DEFAULT_PROTOCOL, SyncAutolink} from '../editor/autolink'
+import {DEFAULT_PROTOCOL, linkifyUrls, SyncAutolink} from '../editor/autolink'
 import {EMOJI_ENABLED} from '../editor/emoji/emoji-enabled'
 import {EmojiExtension} from '../editor/emoji/emoji-extension'
 import {FloatingFormatMenu} from '../editor/floating-format-menu'
@@ -207,6 +207,9 @@ export function useTextEditor(props: {
           if (available > 0 && text.length > 0) {
             const croppedText = text.slice(0, available)
             editor.commands.insertContent(croppedText)
+            // This insert is a command, not a paste transaction, so the on-paste plugin doesn't see
+            // it. Link its URLs here instead.
+            linkifyUrls(editor)
           }
           return true
         }