diff --git a/.github/workflows/r_nightly.yml b/.github/workflows/r_nightly.yml
index 7c52672c1cd..4e12fce9545 100644
--- a/.github/workflows/r_nightly.yml
+++ b/.github/workflows/r_nightly.yml
@@ -1,193 +1,217 @@
-# Licensed to the Apache Software Foundation (ASF) under one
-# or more contributor license agreements.  See the NOTICE file
-# distributed with this work for additional information
-# regarding copyright ownership.  The ASF licenses this file
-# to you under the Apache License, Version 2.0 (the
-# "License"); you may not use this file except in compliance
-# with the License.  You may obtain a copy of the License at
-#
-#   http://www.apache.org/licenses/LICENSE-2.0
-#
-# Unless required by applicable law or agreed to in writing,
-# software distributed under the License is distributed on an
-# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
-# KIND, either express or implied.  See the License for the
-# specific language governing permissions and limitations
-# under the License.
-
-name: Upload R Nightly builds
-# This workflow downloads the (nightly) binaries created in crossbow and uploads them
-# to nightlies.apache.org. Due to authorization requirements, this upload can't be done 
-# from the crossbow repository.
-
-on:
-  workflow_dispatch:
-    inputs:
-      prefix:
-        description: Job prefix to use.
-        required: false
-        default: ''
-      keep:
-        description: Number of versions to keep.
-        required: false
-        default: 14
-
-  schedule:
-    #Crossbow packaging runs at 0 8 * * *
-    - cron: '0 14 * * *'
-
-permissions:
-  contents: read
-
-jobs:
-  upload:
-    if: github.repository == 'apache/arrow'
-    runs-on: ubuntu-latest
-    steps:
-      - name: Checkout Arrow
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
-        with:
-          fetch-depth: 1
-          path: arrow
-          repository: apache/arrow
-          ref: main
-          submodules: recursive
-      - name: Checkout Crossbow
-        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
-        with:
-          fetch-depth: 0
-          path: crossbow
-          repository: ursacomputing/crossbow
-          ref: main
-      - name: Set up Python
+# Licensed to the Apache Software Foundation (ASF) under one
+# or more contributor license agreements.  See the NOTICE file
+# distributed with this work for additional information
+# regarding copyright ownership.  The ASF licenses this file
+# to you under the Apache License, Version 2.0 (the
+# "License"); you may not use this file except in compliance
+# with the License.  You may obtain a copy of the License at
+#
+#   http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing,
+# software distributed under the License is distributed on an
+# "AS IS" BASIS, WITHOUT WARRANTIES OR CONDITIONS OF ANY
+# KIND, either express or implied.  See the License for the
+# specific language governing permissions and limitations
+# under the License.
+
+name: Upload R Nightly builds
+# This workflow downloads the (nightly) binaries created in crossbow and uploads them
+# to nightlies.apache.org. Due to authorization requirements, this upload can't be done
+# from the crossbow repository.
+
+on:
+  workflow_dispatch:
+    inputs:
+      prefix:
+        description: Job prefix to use.
+        required: false
+        default: ''
+      keep:
+        description: Number of versions to keep.
+        required: false
+        default: 14
+
+  schedule:
+    #Crossbow packaging runs at 0 8 * * *
+    - cron: '0 14 * * *'
+
+permissions:
+  contents: read
+
+jobs:
+  upload:
+    if: github.repository == 'apache/arrow'
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout Arrow
+        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        with:
+          fetch-depth: 1
+          path: arrow
+          repository: apache/arrow
+          ref: main
+          submodules: recursive
+      - name: Checkout Crossbow
+        uses: actions/checkout@08c6903cd8c0fde910a37f88322edcfb5dd907a8 # v5.0.0
+        with:
+          fetch-depth: 0
+          path: crossbow
+          repository: ursacomputing/crossbow
+          ref: main
+      - name: Set up Python
         uses: actions/setup-python@e797f83bcb11b83ae66e0230d6156d7c80228e7c # v6.0.0
-        with:
-          cache: 'pip'
-          python-version: 3.12
-      - name: Install Archery
-        shell: bash
-        run: pip install -e arrow/dev/archery[all]
-      - run: mkdir -p binaries
-      - name: Download Artifacts
-        env:
-          PREFIX: ${{ github.event.inputs.prefix || ''}}
-        run: |
-          if [ -z $PREFIX ]; then
-            PREFIX=nightly-packaging-$(date +%Y-%m-%d)-0
-          fi
-          echo $PREFIX
-
-          archery crossbow download-artifacts -f r-binary-packages -t binaries $PREFIX
-
-          if [ -n "$(ls -A binaries/*/*/)" ]; then
-            echo "Found files!"
-          else
-            echo "No files found. Stopping upload."
-            exit 1
-          fi
-      - name: Cache Repo
-        uses: actions/cache@v4
-        with:
-          path: repo
-          key: r-nightly-${{ github.run_id }}
-          restore-keys: r-nightly-
-      - name: Sync from Remote
-        uses: ./arrow/.github/actions/sync-nightlies
-        with:
-          switches: -avzh --update --delete --progress
-          local_path: repo
-          remote_path: ${{ secrets.NIGHTLIES_RSYNC_PATH }}/arrow/r
-          remote_host: ${{ secrets.NIGHTLIES_RSYNC_HOST }}
-          remote_port: ${{ secrets.NIGHTLIES_RSYNC_PORT }}
-          remote_user: ${{ secrets.NIGHTLIES_RSYNC_USER }}
-          remote_key: ${{ secrets.NIGHTLIES_RSYNC_KEY }}
-          remote_host_key: ${{ secrets.NIGHTLIES_RSYNC_HOST_KEY }}
-      - run: tree repo
-      - uses: r-lib/actions/setup-r@v2
-      - name: Build Repository
-        shell: Rscript {0}
-        run: |
-          # folder that we sync to nightlies.apache.org
-          repo_root <- "repo"
-          # The binaries are in a nested dir
-          # so we need to find the correct path.
-          art_path <- list.files("binaries",
-            recursive = TRUE,
-            include.dirs = TRUE,
-            pattern = "r-binary-packages$",
-            full.names = TRUE
-          )
-
-          current_path <- list.files(art_path, full.names = TRUE, recursive = TRUE)
-          files <- sub("r-(pkg|lib)", repo_root, current_path)
-
-          # decode contrib.url from artifact name:
-          # bin__windows__contrib__4.1 -> bin/windows/contrib/4.1
-          new_paths <- gsub("__", "/", files)
-          # strip superfluous nested dirs
-          new_paths <- sub(art_path, ".", new_paths)
-          dirs <- dirname(new_paths)
-          sapply(dirs, dir.create, recursive = TRUE, showWarnings = FALSE)
-
-          # overwrite allows us to "force push" a new version with the same name
-          copy_result <- file.copy(current_path, new_paths, overwrite = TRUE)
-
-          if (!all(copy_result)) {
-            stop("There was an issue while copying the files!")
-          }
-      - name: Prune Repository
-        shell: bash
-        env:
-          KEEP: ${{ github.event.inputs.keep || 14 }}
-        run: |   
-          prune() {
-            # list files  | retain $KEEP newest files | delete everything else
-            ls -t $1/arrow* | tail -n +$((KEEP + 1)) | xargs --no-run-if-empty rm 
-          }
-
-          # find leaf sub dirs
-          repo_dirs=$(find repo -type d -links 2)
-
-          # We want to retain $keep (14) versions of each pkg/lib so we call
-          # prune on each leaf dir and not on repo/.
-          for dir in ${repo_dirs[@]}; do
-            prune $dir
-          done
-      - name: Update Repository Index
-        shell: Rscript {0}
-        run: |
-          # folder that we sync to nightlies.apache.org
-          repo_root <- "repo"
-          tools::write_PACKAGES(file.path(repo_root, "src/contrib"),
-            type = "source",
-            verbose = TRUE,
-            latestOnly = FALSE
-          )
-
-          repo_dirs <- list.dirs(repo_root)
-          # find dirs with binary R packages: e.g. */contrib/4.1
-          pkg_dirs <- grep(".+contrib\\/\\d.+", repo_dirs, value = TRUE)
-
-
-          for (dir in pkg_dirs) {
-            on_win <- grepl("windows", dir)
-            tools::write_PACKAGES(dir,
-              type = ifelse(on_win, "win.binary", "mac.binary"),
-              verbose = TRUE,
-              latestOnly = FALSE
-            )
-          }
-      - name: Show repo contents
-        run: tree repo
-      - name: Sync to Remote
-        uses: ./arrow/.github/actions/sync-nightlies
-        with:
-          upload: true
-          switches: -avzh --update --delete --progress
-          local_path: repo
-          remote_path: ${{ secrets.NIGHTLIES_RSYNC_PATH }}/arrow/r
-          remote_host: ${{ secrets.NIGHTLIES_RSYNC_HOST }}
-          remote_port: ${{ secrets.NIGHTLIES_RSYNC_PORT }}
-          remote_user: ${{ secrets.NIGHTLIES_RSYNC_USER }}
-          remote_key: ${{ secrets.NIGHTLIES_RSYNC_KEY }}
-          remote_host_key: ${{ secrets.NIGHTLIES_RSYNC_HOST_KEY }}
+        with:
+          cache: 'pip'
+          python-version: 3.12
+      - name: Install Archery
+        shell: bash
+        run: pip install -e arrow/dev/archery[all]
+      - run: mkdir -p binaries
+      - name: Download Artifacts
+        env:
+          PREFIX: ${{ github.event.inputs.prefix || ''}}
+        run: |
+          if [ -z $PREFIX ]; then
+            PREFIX=nightly-packaging-$(date +%Y-%m-%d)-0
+          fi
+          echo $PREFIX
+
+          archery crossbow download-artifacts -f r-binary-packages -t binaries $PREFIX
+
+          if [ -n "$(ls -A binaries/*/*/)" ]; then
+            echo "Found files!"
+          else
+            echo "No files found. Stopping upload."
+            exit 1
+          fi
+      - name: Cache Repo
+        uses: actions/cache@v4
+        with:
+          path: repo
+          key: r-nightly-${{ github.run_id }}
+          restore-keys: r-nightly-
+      - name: Sync from Remote
+        uses: ./arrow/.github/actions/sync-nightlies
+        with:
+          switches: -avzh --update --delete --progress
+          local_path: repo
+          remote_path: ${{ secrets.NIGHTLIES_RSYNC_PATH }}/arrow/r
+          remote_host: ${{ secrets.NIGHTLIES_RSYNC_HOST }}
+          remote_port: ${{ secrets.NIGHTLIES_RSYNC_PORT }}
+          remote_user: ${{ secrets.NIGHTLIES_RSYNC_USER }}
+          remote_key: ${{ secrets.NIGHTLIES_RSYNC_KEY }}
+          remote_host_key: ${{ secrets.NIGHTLIES_RSYNC_HOST_KEY }}
+      - run: tree repo
+      - uses: r-lib/actions/setup-r@v2
+      - name: Build Repository
+        shell: Rscript {0}
+        run: |
+          # folder that we sync to nightlies.apache.org
+          repo_root <- "repo"
+          # The binaries are in a nested dir
+          # so we need to find the correct path.
+          art_path <- list.files("binaries",
+            recursive = TRUE,
+            include.dirs = TRUE,
+            pattern = "r-binary-packages$",
+            full.names = TRUE
+          )
+
+          current_pkg_path <- list.files(art_path,
+            full.names = TRUE,
+            pattern = "r-pkg",
+            recursive = TRUE
+          )
+          current_lib_path <- list.files(art_path,
+            full.names = TRUE,
+            pattern = "r-lib",
+            recursive = TRUE
+          )
+          files <- c(
+            sub("r-pkg", repo_root, current_pkg_path),
+            sub("r-lib", paste0(repo_root, "__r-lib"), current_lib_path),
+          )
+
+          # decode contrib.url from artifact name:
+          # bin__windows__contrib__4.1 -> bin/windows/contrib/4.1
+          new_paths <- gsub("__", "/", files)
+          # strip superfluous nested dirs
+          new_paths <- sub(art_path, ".", new_paths)
+          dirs <- dirname(new_paths)
+          sapply(dirs, dir.create, recursive = TRUE, showWarnings = FALSE)
+
+          # overwrite allows us to "force push" a new version with the same name
+          copy_result <- file.copy(current_path, new_paths, overwrite = TRUE)
+
+          if (!all(copy_result)) {
+            stop("There was an issue while copying the files!")
+          }
+      - name: Prune Repository
+        shell: bash
+        env:
+          KEEP: ${{ github.event.inputs.keep || 14 }}
+        run: |
+          prune() {
+            # list files  | retain $KEEP newest files | delete everything else
+            ls -t "$@" | tail -n +$((KEEP + 1)) | xargs --no-run-if-empty rm
+          }
+
+          # find leaf sub dirs
+          repo_dirs=$(find repo -type d -links 2)
+
+          # Old packages: repo/libarrow/bin/${TARGET}/arrow-${VERSION}.zip
+          #
+          # We want to retain $keep (14) versions of each pkg/lib so we call
+          # prune on each leaf dir and not on repo/.
+          for dir in "${repo_dirs[@]}"; do
+            prune $dir/arrow*
+          done
+
+          # New packages: repo/libarrow/${TARGET}-arrow-${VERSION}.zip
+          prune repo/libarrow/r-libarrow-darwin-arm64-openssl-1.1-* || :
+          prune repo/libarrow/r-libarrow-darwin-arm64-openssl-3.0-* || :
+          prune repo/libarrow/r-libarrow-darwin-x86_64-openssl-1.1-* || :
+          prune repo/libarrow/r-libarrow-darwin-x86_64-openssl-3.0-* || :
+          prune repo/libarrow/r-libarrow-linux-x86_64-openssl-1.0-* || :
+          prune repo/libarrow/r-libarrow-linux-x86_64-openssl-1.1-* || :
+          prune repo/libarrow/r-libarrow-linux-x86_64-openssl-3.0-* || :
+          prune repo/libarrow/r-libarrow-windows-x86_64-* || :
+      - name: Update Repository Index
+        shell: Rscript {0}
+        run: |
+          # folder that we sync to nightlies.apache.org
+          repo_root <- "repo"
+          tools::write_PACKAGES(file.path(repo_root, "src/contrib"),
+            type = "source",
+            verbose = TRUE,
+            latestOnly = FALSE
+          )
+
+          repo_dirs <- list.dirs(repo_root)
+          # find dirs with binary R packages: e.g. */contrib/4.1
+          pkg_dirs <- grep(".+contrib\\/\\d.+", repo_dirs, value = TRUE)
+
+
+          for (dir in pkg_dirs) {
+            on_win <- grepl("windows", dir)
+            tools::write_PACKAGES(dir,
+              type = ifelse(on_win, "win.binary", "mac.binary"),
+              verbose = TRUE,
+              latestOnly = FALSE
+            )
+          }
+      - name: Show repo contents
+        run: tree repo
+      - name: Sync to Remote
+        uses: ./arrow/.github/actions/sync-nightlies
+        with:
+          upload: true
+          switches: -avzh --update --delete --progress
+          local_path: repo
+          remote_path: ${{ secrets.NIGHTLIES_RSYNC_PATH }}/arrow/r
+          remote_host: ${{ secrets.NIGHTLIES_RSYNC_HOST }}
+          remote_port: ${{ secrets.NIGHTLIES_RSYNC_PORT }}
+          remote_user: ${{ secrets.NIGHTLIES_RSYNC_USER }}
+          remote_key: ${{ secrets.NIGHTLIES_RSYNC_KEY }}
+          remote_host_key: ${{ secrets.NIGHTLIES_RSYNC_HOST_KEY }}