diff --git a/NEWS.md b/NEWS.md
index a85b0ff5f..d56571420 100644
--- a/NEWS.md
+++ b/NEWS.md
@@ -1,5 +1,8 @@
 # devtools (development version)
 
+* `dr_devtools()` now uses the same endpoint to detect the current RStudio
+  version as the IDE (#2050).
+
 * `release()` now works again when `pkg` is not the current working directory
   (#1974).
 
diff --git a/R/doctor.R b/R/doctor.R
index bcb7fddd5..de65004e6 100644
--- a/R/doctor.R
+++ b/R/doctor.R
@@ -2,16 +2,39 @@
 #' @importFrom memoise memoise
 NULL
 
-.rstudio_release <- function() {
-  url <- "http://s3.amazonaws.com/rstudio-desktop/current.ver"
-  res <- readLines(url, warn = FALSE)
-  if (length(res) != 1) {
-    return(0)
+check_for_rstudio_updates <- function(os = tolower(Sys.info()[["sysname"]]), version = rstudioapi::getVersion(), in_rstudio = rstudioapi::isAvailable()) {
+
+  if (!in_rstudio) {
+    return()
   }
-  numeric_version(res)
-}
 
-rstudio_release <- memoise::memoise(.rstudio_release)
+  url <- sprintf("https://www.rstudio.org/links/check_for_update?version=%s&os=%s&format=kvp", version, os, "kvp")
+
+  tmp <- tempfile()
+  on.exit(unlink(tmp))
+  utils::download.file(url, tmp, quiet = TRUE)
+  result <- readLines(tmp, warn = FALSE)
+
+  result <- strsplit(result, "&")[[1]]
+
+  result <- strsplit(result, "=")
+
+  # If no values then we are current
+  if (length(result[[1]]) == 1) {
+    return()
+  }
+
+  nms <- vcapply(result, `[[`, 1)
+  values <- vcapply(result, function(x) URLdecode(x[[2]]))
+
+  result <- stats::setNames(values, nms)
+
+  if (!nzchar(result[["update-version"]])) {
+    return()
+  }
+
+  sprintf("* RStudio is out of date, %s. Download at: %s", result[["update-message"]], result[["update-url"]])
+}
 
 .r_release <- function() {
   check_suggested("rversions")
@@ -51,16 +74,7 @@ dr_devtools <- function() {
     )
   }
 
-  if (rstudioapi::isAvailable()) {
-    rel <- rstudio_release()
-    cur <- rstudioapi::getVersion()
-
-    if (cur < rel) {
-      msg[["rstudio"]] <- paste0(
-        "* RStudio is out of date (", cur, " vs ", rel, ")"
-      )
-    }
-  }
+  msg[["rstudio"]] <- check_for_rstudio_updates("mac", "1.0.0", TRUE)
 
   doctor("devtools", msg)
 }
diff --git a/R/utils.R b/R/utils.R
index c280478ff..05b91774a 100644
--- a/R/utils.R
+++ b/R/utils.R
@@ -174,3 +174,7 @@ escape_special_regex <- function(x) {
 has_dev_remotes <- function(pkg) {
   !is.null(pkg[["remotes"]])
 }
+
+vcapply <- function(x, FUN, ...) {
+  vapply(x, FUN, FUN.VALUE = character(1), ...)
+}
diff --git a/tests/testthat/test-doctor.R b/tests/testthat/test-doctor.R
new file mode 100644
index 000000000..06caf8201
--- /dev/null
+++ b/tests/testthat/test-doctor.R
@@ -0,0 +1,12 @@
+test_that("check_for_rstudio_updates", {
+  # returns nothing rstudio not available
+  expect_null(check_for_rstudio_updates("mac", "1.0.0", FALSE))
+
+  # returns nothing if the version is ahead of the current version
+  expect_null(check_for_rstudio_updates("mac", "1000.0.0", TRUE))
+
+  # returns something if the version is behind of the current version
+  res <- check_for_rstudio_updates("mac", "0.0.1", TRUE)
+  expect_match(res, "RStudio is out of date")
+  expect_match(res, "Download at")
+})