diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index 5cabc33a..02bc1df3 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -2,7 +2,7 @@ We welcome contributions to the **httpuv** package. To submit a contribution:
 
 1. [Fork](https://github.com/rstudio/httpuv/fork) the repository and make your changes.
 
-2. Submit a [pull request](https://help.github.com/articles/using-pull-requests).
+2. Submit a [pull request](https://docs.github.com/en/pull-requests/reference/pull-requests).
 
 3. You will be prompted to read and agree to the "RStudio Corporate and Individual Contributor Agreement."
 
diff --git a/NEWS.md b/NEWS.md
index ad468432..20e30c57 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -4,6 +4,8 @@
 
 * Fixed #439: Multiple `Cookie` request headers are now combined with `"; "` instead of `","`, as required by RFC 6265 (thanks to @andyquinterom, #440).
 
+* Updated stale URLs in the documentation and comments (thanks to @vikram-rawat, #286, #444).
+
 # httpuv 1.6.17
 
 * Closed #426: Uses native symbol registration for calls into compiled code, resulting in performance gains from not having to perform a lookup on each call. (#427)
diff --git a/R/httpuv-package.R b/R/httpuv-package.R
index a0abe642..9d059743 100644
--- a/R/httpuv-package.R
+++ b/R/httpuv-package.R
@@ -2,7 +2,7 @@
 #'
 #' Allows R code to listen for and interact with HTTP and WebSocket clients, so
 #' you can serve web traffic directly out of your R process. Implementation is
-#' based on [libuv](https://github.com/joyent/libuv) and
+#' based on [libuv](https://github.com/libuv/libuv) and
 #' [http-parser](https://github.com/nodejs/http-parser).
 #'
 #' This is a low-level library that provides little more than network I/O and
diff --git a/R/random_port.R b/R/random_port.R
index 6fb6affb..e1cbc423 100644
--- a/R/random_port.R
+++ b/R/random_port.R
@@ -60,7 +60,7 @@ error_unavailable_port <- function(message = "Cannot find an available port.") {
 }
 
 # Ports that are considered unsafe by Chrome
-# http://superuser.com/questions/188058/which-ports-are-considered-unsafe-on-chrome
+# https://superuser.com/questions/188058/which-ports-are-considered-unsafe-on-chrome
 # https://github.com/rstudio/shiny/issues/1784
 unsafe_ports <- c(
   1,
diff --git a/README.md b/README.md
index 0a0d2fdc..f17bd074 100644
--- a/README.md
+++ b/README.md
@@ -21,7 +21,7 @@ install.packages("httpuv")
 pak::pak("rstudio/httpuv")
 ```
 
-Since httpuv contains C code, you'll need to make sure you're set up to install packages with compiled code. Follow the instructions at http://www.rstudio.com/ide/docs/packages/prerequisites
+Since httpuv contains C code, you'll need to make sure you're set up to install packages with compiled code. Follow the instructions at https://support.posit.co/hc/en-us/articles/200486498-Package-Development-Prerequisites
 
 httpuv may optionally be built using a `libuv` system package, which you can install prior to installing the R package. It goes by different names on different package managers: `libuv1-dev` (deb), `libuv-devel` (rpm), `libuv` (brew). Version 1.43 or greater is required. If `libuv` is not found on the system, it will be built from source along with the R package.
 
diff --git a/man/httpuv-package.Rd b/man/httpuv-package.Rd
index 2c6ee4d2..53919e97 100644
--- a/man/httpuv-package.Rd
+++ b/man/httpuv-package.Rd
@@ -11,7 +11,7 @@ HTTP and WebSocket server
 \details{
 Allows R code to listen for and interact with HTTP and WebSocket clients, so
 you can serve web traffic directly out of your R process. Implementation is
-based on \href{https://github.com/joyent/libuv}{libuv} and
+based on \href{https://github.com/libuv/libuv}{libuv} and
 \href{https://github.com/nodejs/http-parser}{http-parser}.
 
 This is a low-level library that provides little more than network I/O and
diff --git a/tests/testthat/test-static-paths.R b/tests/testthat/test-static-paths.R
index f5c5d015..6c58d6af 100644
--- a/tests/testthat/test-static-paths.R
+++ b/tests/testthat/test-static-paths.R
@@ -773,7 +773,7 @@ test_that("Last-Modified and If-Modified-Since headers", {
   # A 304 response should contain only the following headers (and must contain
   # them if the corresponding 200 response would have them):
   # Cache-Control, Content-Location, Date, ETag, Expires, Vary
-  # https://httpstatuses.com/304
+  # https://httpstatuses.io/304
   expect_identical(
     h[c("cache-control", "etag")],
     h1[c("cache-control", "etag")]