diff --git a/rip/cli.py b/rip/cli.py
index 06392ce..3c337a0 100644
--- a/rip/cli.py
+++ b/rip/cli.py
@@ -18,6 +18,7 @@ logging.basicConfig(level="WARNING")
 logger = logging.getLogger("streamrip")
 
 outdated = False
+newest_version = __version__
 
 
 class DownloadCommand(Command):
@@ -86,11 +87,38 @@ class DownloadCommand(Command):
 
         update_check.join()
         if outdated:
+            import subprocess
+            import re
+
             self.line(
-                "<info>A new version of streamrip is available! Run</info> "
-                "<cmd>pip3 install streamrip --upgrade to update</cmd>"
+                f"<info>Updating streamrip to <title>v{newest_version}</title>...</info>\n"
             )
 
+            # update in background
+            update_p = subprocess.Popen(
+                ["pip3", "install", "streamrip", "--upgrade"],
+                stdout=subprocess.PIPE,
+                stderr=subprocess.PIPE,
+            )
+
+            md_header = re.compile(r"#\s+(.+)")
+            bullet_point = re.compile(r"-\s*(.+)")
+            code = re.compile(r"`([^`]+)`")
+            issue_reference = re.compile(r"(#\d+)")
+
+            release_notes = requests.get(
+                "https://api.github.com/repos/nathom/streamrip/releases/latest"
+            ).json()["body"]
+
+            release_notes = md_header.sub(r"<header>\1</header>", release_notes)
+            release_notes = bullet_point.sub(r"<options=bold>•</> \1", release_notes)
+            release_notes = code.sub(r"<cmd>\1</cmd>", release_notes)
+            release_notes = issue_reference.sub(r"<options=bold>\1</>", release_notes)
+
+            self.line(release_notes)
+
+            update_p.wait()
+
         return 0
 
 
@@ -448,6 +476,7 @@ class Application(BaseApplication):
         formatter.set_style("path", Style("green", options=["bold"]))
         formatter.set_style("cmd", Style("magenta"))
         formatter.set_style("title", Style("yellow", options=["bold"]))
+        formatter.set_style("header", Style("yellow", options=["bold", "underline"]))
         io.output.set_formatter(formatter)
         io.error_output.set_formatter(formatter)
 
@@ -491,8 +520,10 @@ def clean_options(*opts):
 
 def is_outdated():
     global outdated
+    global newest_version
     r = requests.get("https://pypi.org/pypi/streamrip/json").json()
-    outdated = r["info"]["version"] != __version__
+    newest_version = r["info"]["version"]
+    outdated = newest_version != __version__
 
 
 def main():