diff --git a/r/tools/update-checksums.R b/r/tools/update-checksums.R
index 2aa9df317166f..8b9f1e6959cfd 100644
--- a/r/tools/update-checksums.R
+++ b/r/tools/update-checksums.R
@@ -38,6 +38,7 @@ if (!file.exists(tasks_yml)) {
   stop("Run this script from the r/ directory of the arrow repo")
 }
 
+cat("Extracting libarrow binary paths from tasks.yml\n")
 # Get the libarrow binary paths from the tasks.yml file
 binary_paths <- readLines(tasks_yml) |>
   grep("r-lib__libarrow", x = _, value = TRUE) |>
@@ -53,15 +54,19 @@ for (path in binary_paths) {
   sha_path <- paste0(path, ".sha512")
   file <- file.path("tools/checksums", sha_path)
   dirname(file) |> dir.create(path = _, recursive = TRUE, showWarnings = FALSE)
-
+  
+  cat(paste0("Downloading ", sha_path, "\n"))
   url <- sprintf(artifactory_root, VERSION, sha_path)
   download.file(url, file, quiet = TRUE, cacheOK = FALSE)
 
   if (grepl("windows", path)) {
+    cat(paste0("Converting ", path, " to windows style line endings\n"))
     # UNIX style line endings cause errors with mysys2 sha512sum
-    sed_status <- system2("sed", args = c("-i", "s/\\r//", file))
+    sed_status <- system2("sed", args = c("-i", "s/\\\\r//", file))
     if (sed_status != 0) {
       stop("Failed to remove \\r from windows checksum file. Exit code: ", sed_status)
     }
   }
 }
+
+cat("Checksums updated successfully!\n")