diff --git a/nip27.test.ts b/nip27.test.ts
index 02de0c0..141a8ad 100644
--- a/nip27.test.ts
+++ b/nip27.test.ts
@@ -1,68 +1,77 @@
 import { test, expect } from 'bun:test'
-import { matchAll, replaceAll } from './nip27.ts'
+import { parse } from './nip27.ts'
 
-test('matchAll', () => {
-  const result = matchAll(
-    'Hello nostr:npub108pv4cg5ag52nq082kd5leu9ffrn2gdg6g4xdwatn73y36uzplmq9uyev6!\n\nnostr:note1gmtnz6q2m55epmlpe3semjdcq987av3jvx4emmjsa8g3s9x7tg4sclreky',
-  )
+test('first: parse simple content with 1 url and 1 nostr uri', () => {
+  const content = `nostr:npub1hpslpc8c5sp3e2nhm2fr7swsfqpys5vyjar5dwpn7e7decps6r8qkcln63 check out my profile:nostr:npub1xtscya34g58tk0z605fvr788k263gsu6cy9x0mhnm87echrgufzsevkk5s; and this cool image https://images.com/image.jpg`
+  const blocks = Array.from(parse(content))
 
-  expect([...result]).toEqual([
-    {
-      uri: 'nostr:npub108pv4cg5ag52nq082kd5leu9ffrn2gdg6g4xdwatn73y36uzplmq9uyev6',
-      value: 'npub108pv4cg5ag52nq082kd5leu9ffrn2gdg6g4xdwatn73y36uzplmq9uyev6',
-      decoded: {
-        type: 'npub',
-        data: '79c2cae114ea28a981e7559b4fe7854a473521a8d22a66bbab9fa248eb820ff6',
-      },
-      start: 6,
-      end: 75,
-    },
-    {
-      uri: 'nostr:note1gmtnz6q2m55epmlpe3semjdcq987av3jvx4emmjsa8g3s9x7tg4sclreky',
-      value: 'note1gmtnz6q2m55epmlpe3semjdcq987av3jvx4emmjsa8g3s9x7tg4sclreky',
-      decoded: {
-        type: 'note',
-        data: '46d731680add2990efe1cc619dc9b8014feeb23261ab9dee50e9d11814de5a2b',
-      },
-      start: 78,
-      end: 147,
-    },
+  expect(blocks).toEqual([
+    { type: 'reference', pointer: { pubkey: 'b861f0e0f8a4031caa77da923f41d04802485184974746b833f67cdce030d0ce' } },
+    { type: 'text', text: ' check out my profile:' },
+    { type: 'reference', pointer: { pubkey: '32e1827635450ebb3c5a7d12c1f8e7b2b514439ac10a67eef3d9fd9c5c68e245' } },
+    { type: 'text', text: '; and this cool image ' },
+    { type: 'image', url: 'https://images.com/image.jpg' },
   ])
 })
 
-test('matchAll with an invalid nip19', () => {
-  const result = matchAll(
-    'Hello nostr:npub129tvj896hqqkljerxkccpj9flshwnw999v9uwn9lfmwlj8vnzwgq9y5llnpub1rujdpkd8mwezrvpqd2rx2zphfaztqrtsfg6w3vdnlj!\n\nnostr:note1gmtnz6q2m55epmlpe3semjdcq987av3jvx4emmjsa8g3s9x7tg4sclreky',
-  )
+test('second: parse content with 3 urls of different types', () => {
+  const content = `:wss://oa.ao; this was a relay and now here's a video -> https://videos.com/video.mp4! and some music:
+http://music.com/song.mp3
+and a regular link: https://regular.com/page?ok=true. and now a broken link: https://kjxkxk and a broken nostr ref: nostr:nevent1qqsr0f9w78uyy09qwmjt0kv63j4l7sxahq33725lqyyp79whlfjurwspz4mhxue69uhh56nzv34hxcfwv9ehw6nyddhq0ag9xg and a fake nostr ref: nostr:llll ok but finally https://ok.com!`
+  const blocks = Array.from(parse(content))
 
-  expect([...result]).toEqual([
+  expect(blocks).toEqual([
+    { type: 'text', text: ':' },
+    { type: 'relay', url: 'wss://oa.ao/' },
+    { type: 'text', text: "; this was a relay and now here's a video -> " },
+    { type: 'video', url: 'https://videos.com/video.mp4' },
+    { type: 'text', text: '! and some music:\n' },
+    { type: 'audio', url: 'http://music.com/song.mp3' },
+    { type: 'text', text: '\nand a regular link: ' },
+    { type: 'url', url: 'https://regular.com/page?ok=true' },
     {
-      decoded: {
-        data: '46d731680add2990efe1cc619dc9b8014feeb23261ab9dee50e9d11814de5a2b',
-        type: 'note',
-      },
-      end: 193,
-      start: 124,
-      uri: 'nostr:note1gmtnz6q2m55epmlpe3semjdcq987av3jvx4emmjsa8g3s9x7tg4sclreky',
-      value: 'note1gmtnz6q2m55epmlpe3semjdcq987av3jvx4emmjsa8g3s9x7tg4sclreky',
+      type: 'text',
+      text: '. and now a broken link: https://kjxkxk and a broken nostr ref: nostr:nevent1qqsr0f9w78uyy09qwmjt0kv63j4l7sxahq33725lqyyp79whlfjurwspz4mhxue69uhh56nzv34hxcfwv9ehw6nyddhq0ag9xg and a fake nostr ref: nostr:llll ok but finally ',
     },
+    { type: 'url', url: 'https://ok.com/' },
+    { type: 'text', text: '!' },
   ])
 })
 
-test('replaceAll', () => {
-  const content =
-    'Hello nostr:npub108pv4cg5ag52nq082kd5leu9ffrn2gdg6g4xdwatn73y36uzplmq9uyev6!\n\nnostr:note1gmtnz6q2m55epmlpe3semjdcq987av3jvx4emmjsa8g3s9x7tg4sclreky'
+test('third: parse complex content with 4 nostr uris and 3 urls', () => {
+  const content = `Look at these profiles nostr:npub1xtscya34g58tk0z605fvr788k263gsu6cy9x0mhnm87echrgufzsevkk5s nostr:nprofile1qqs8z4gwdjp6jwqlxhzk35dgpcgl50swljtal58q796f9ghdkexr02gppamhxue69uhhzamfv46jucm0d574e4uy check this event nostr:nevent1qqsr0f9w78uyy09qwmjt0kv63j4l7sxahq33725lqyyp79whlfjurwspz4mhxue69uhh56nzv34hxcfwv9ehw6nyddhq0ag9xl
+    here's an image https://example.com/pic.png and another profile nostr:npub1xtscya34g58tk0z605fvr788k263gsu6cy9x0mhnm87echrgufzsevkk5s
+    with a video https://example.com/vid.webm and finally https://example.com/docs`
+  const blocks = Array.from(parse(content))
 
-  const result = replaceAll(content, ({ decoded, value }) => {
-    switch (decoded.type) {
-      case 'npub':
-        return '@alex'
-      case 'note':
-        return '!1234'
-      default:
-        return value
-    }
-  })
-
-  expect(result).toEqual('Hello @alex!\n\n!1234')
+  expect(blocks).toEqual([
+    { type: 'text', text: 'Look at these profiles ' },
+    { type: 'reference', pointer: { pubkey: '32e1827635450ebb3c5a7d12c1f8e7b2b514439ac10a67eef3d9fd9c5c68e245' } },
+    { type: 'text', text: ' ' },
+    {
+      type: 'reference',
+      pointer: {
+        pubkey: '71550e6c83a9381f35c568d1a80e11fa3e0efc97dfd0e0f17492a2edb64c37a9',
+        relays: ['wss://qwieu.com'],
+      },
+    },
+    { type: 'text', text: ' check this event ' },
+    {
+      type: 'reference',
+      pointer: {
+        id: '37a4aef1f8423ca076e4b7d99a8cabff40ddb8231f2a9f01081f15d7fa65c1ba',
+        relays: ['wss://zjbdksa.aswjdkn'],
+        author: undefined,
+        kind: undefined,
+      },
+    },
+    { type: 'text', text: "\n    here's an image " },
+    { type: 'image', url: 'https://example.com/pic.png' },
+    { type: 'text', text: ' and another profile ' },
+    { type: 'reference', pointer: { pubkey: '32e1827635450ebb3c5a7d12c1f8e7b2b514439ac10a67eef3d9fd9c5c68e245' } },
+    { type: 'text', text: '\n    with a video ' },
+    { type: 'video', url: 'https://example.com/vid.webm' },
+    { type: 'text', text: ' and finally ' },
+    { type: 'url', url: 'https://example.com/docs' },
+  ])
 })
diff --git a/nip27.ts b/nip27.ts
index d45224c..7c5d61c 100644
--- a/nip27.ts
+++ b/nip27.ts
@@ -1,63 +1,169 @@
-import { decode } from './nip19.ts'
-import { NOSTR_URI_REGEX, type NostrURI } from './nip21.ts'
+import { AddressPointer, EventPointer, ProfilePointer, decode } from './nip19.ts'
 
-/** Regex to find NIP-21 URIs inside event content. */
-export const regex = (): RegExp => new RegExp(`\\b${NOSTR_URI_REGEX.source}\\b`, 'g')
+export type Block =
+  | {
+      type: 'text'
+      text: string
+    }
+  | {
+      type: 'reference'
+      pointer: ProfilePointer | AddressPointer | EventPointer
+    }
+  | {
+      type: 'url'
+      url: string
+    }
+  | {
+      type: 'relay'
+      url: string
+    }
+  | {
+      type: 'image'
+      url: string
+    }
+  | {
+      type: 'video'
+      url: string
+    }
+  | {
+      type: 'audio'
+      url: string
+    }
 
-/** Match result for a Nostr URI in event content. */
-export interface NostrURIMatch extends NostrURI {
-  /** Index where the URI begins in the event content. */
-  start: number
-  /** Index where the URI ends in the event content. */
-  end: number
-}
+const noCharacter = /\W/m
+const noURLCharacter = /\W |\W$|$|,| /m
 
-/** Find and decode all NIP-21 URIs. */
-export function* matchAll(content: string): Iterable<NostrURIMatch> {
-  const matches = content.matchAll(regex())
+export function* parse(content: string): Iterable<Block> {
+  const max = content.length
+  let prevIndex = 0
+  let index = 0
+  while (index < max) {
+    let u = content.indexOf(':', index)
+    if (u === -1) {
+      // reached end
+      break
+    }
 
-  for (const match of matches) {
-    try {
-      const [uri, value] = match
+    if (content.substring(u - 5, u) === 'nostr') {
+      const m = content.substring(u + 60).match(noCharacter)
+      const end = m ? u + 60 + m.index! : max
+      try {
+        let pointer: ProfilePointer | AddressPointer | EventPointer
+        let { data, type } = decode(content.substring(u + 1, end))
 
-      yield {
-        uri: uri as `nostr:${string}`,
-        value,
-        decoded: decode(value),
-        start: match.index!,
-        end: match.index! + uri.length,
+        switch (type) {
+          case 'npub':
+            pointer = { pubkey: data } as ProfilePointer
+            break
+          case 'nsec':
+          case 'note':
+            // ignore this, treat it as not a valid uri
+            index = end + 1
+            continue
+          default:
+            pointer = data as any
+        }
+
+        if (prevIndex !== u - 5) {
+          yield { type: 'text', text: content.substring(prevIndex, u - 5) }
+        }
+        yield { type: 'reference', pointer }
+        index = end
+        prevIndex = index
+        continue
+      } catch (_err) {
+        // ignore this, not a valid nostr uri
+        index = u + 1
+        continue
       }
-    } catch (_e) {
-      // do nothing
+    } else if (content.substring(u - 5, u) === 'https' || content.substring(u - 4, u) === 'http') {
+      const m = content.substring(u + 4).match(noURLCharacter)
+      const end = m ? u + 4 + m.index! : max
+      const prefixLen = content[u - 1] === 's' ? 5 : 4
+      try {
+        let url = new URL(content.substring(u - prefixLen, end))
+        if (url.hostname.indexOf('.') === -1) {
+          throw new Error('invalid url')
+        }
+
+        if (prevIndex !== u - prefixLen) {
+          yield { type: 'text', text: content.substring(prevIndex, u - prefixLen) }
+        }
+
+        if (
+          url.pathname.endsWith('.png') ||
+          url.pathname.endsWith('.jpg') ||
+          url.pathname.endsWith('.jpeg') ||
+          url.pathname.endsWith('.gif') ||
+          url.pathname.endsWith('.webp')
+        ) {
+          yield { type: 'image', url: url.toString() }
+          index = end
+          prevIndex = index
+          continue
+        }
+        if (
+          url.pathname.endsWith('.mp4') ||
+          url.pathname.endsWith('.avi') ||
+          url.pathname.endsWith('.webm') ||
+          url.pathname.endsWith('.mkv')
+        ) {
+          yield { type: 'video', url: url.toString() }
+          index = end
+          prevIndex = index
+          continue
+        }
+        if (
+          url.pathname.endsWith('.mp3') ||
+          url.pathname.endsWith('.aac') ||
+          url.pathname.endsWith('.ogg') ||
+          url.pathname.endsWith('.opus')
+        ) {
+          yield { type: 'audio', url: url.toString() }
+          index = end
+          prevIndex = index
+          continue
+        }
+
+        yield { type: 'url', url: url.toString() }
+        index = end
+        prevIndex = index
+        continue
+      } catch (_err) {
+        // ignore this, not a valid url
+        index = end + 1
+        continue
+      }
+    } else if (content.substring(u - 3, u) === 'wss' || content.substring(u - 2, u) === 'ws') {
+      const m = content.substring(u + 4).match(noURLCharacter)
+      const end = m ? u + 4 + m.index! : max
+      const prefixLen = content[u - 1] === 's' ? 3 : 2
+      try {
+        let url = new URL(content.substring(u - prefixLen, end))
+        if (url.hostname.indexOf('.') === -1) {
+          throw new Error('invalid ws url')
+        }
+
+        if (prevIndex !== u - prefixLen) {
+          yield { type: 'text', text: content.substring(prevIndex, u - prefixLen) }
+        }
+        yield { type: 'relay', url: url.toString() }
+        index = end
+        prevIndex = index
+        continue
+      } catch (_err) {
+        // ignore this, not a valid url
+        index = end + 1
+        continue
+      }
+    } else {
+      // ignore this, it is nothing
+      index = u + 1
+      continue
     }
   }
-}
 
-/**
- * Replace all occurrences of Nostr URIs in the text.
- *
- * WARNING: using this on an HTML string is potentially unsafe!
- *
- * @example
- * ```ts
- * nip27.replaceAll(event.content, ({ decoded, value }) => {
- *   switch(decoded.type) {
- *     case 'npub':
- *       return renderMention(decoded)
- *     case 'note':
- *       return renderNote(decoded)
- *     default:
- *       return value
- *   }
- * })
- * ```
- */
-export function replaceAll(content: string, replacer: (match: NostrURI) => string): string {
-  return content.replaceAll(regex(), (uri, value: string) => {
-    return replacer({
-      uri: uri as `nostr:${string}`,
-      value,
-      decoded: decode(value),
-    })
-  })
+  if (prevIndex !== max) {
+    yield { type: 'text', text: content.substring(prevIndex) }
+  }
 }