diff --git a/src/bootstrap/lib.rs b/src/bootstrap/lib.rs
index cbdb174c02d97..39d7ea922bced 100644
--- a/src/bootstrap/lib.rs
+++ b/src/bootstrap/lib.rs
@@ -1080,6 +1080,10 @@ impl Build {
     /// done. The file is updated immediately after this function completes.
     pub fn save_toolstate(&self, tool: &str, state: ToolState) {
         if let Some(ref path) = self.config.save_toolstates {
+            if let Some(parent) = path.parent() {
+                // Ensure the parent directory always exists
+                t!(std::fs::create_dir_all(parent));
+            }
             let mut file = t!(fs::OpenOptions::new()
                 .create(true)
                 .read(true)
diff --git a/src/ci/azure-pipelines/auto.yml b/src/ci/azure-pipelines/auto.yml
index 24b07a1b7c950..271c32585449e 100644
--- a/src/ci/azure-pipelines/auto.yml
+++ b/src/ci/azure-pipelines/auto.yml
@@ -140,6 +140,7 @@ jobs:
         IMAGE: x86_64-gnu-aux
       x86_64-gnu-tools:
         IMAGE: x86_64-gnu-tools
+        DEPLOY_TOOLSTATES_JSON: toolstates-linux.json
       x86_64-gnu-debug:
         IMAGE: x86_64-gnu-debug
       x86_64-gnu-nopt:
@@ -262,8 +263,9 @@ jobs:
       # MSVC tools tests
       x86_64-msvc-tools:
         MSYS_BITS: 64
-        SCRIPT: src/ci/docker/x86_64-gnu-tools/checktools.sh x.py /tmp/toolstates.json windows
-        RUST_CONFIGURE_ARGS: --build=x86_64-pc-windows-msvc --save-toolstates=/tmp/toolstates.json
+        SCRIPT: src/ci/docker/x86_64-gnu-tools/checktools.sh x.py /tmp/toolstate/toolstates.json windows
+        RUST_CONFIGURE_ARGS: --build=x86_64-pc-windows-msvc --save-toolstates=/tmp/toolstate/toolstates.json
+        DEPLOY_TOOLSTATES_JSON: toolstates-windows.json
 
       # 32/64-bit MinGW builds.
       #
diff --git a/src/ci/azure-pipelines/steps/run.yml b/src/ci/azure-pipelines/steps/run.yml
index 01858cca50b1c..c82bc6af738a0 100644
--- a/src/ci/azure-pipelines/steps/run.yml
+++ b/src/ci/azure-pipelines/steps/run.yml
@@ -201,37 +201,21 @@ steps:
   condition: and(succeeded(), not(variables.SKIP_JOB))
   displayName: Run build
 
-# If we're a deploy builder, use the `aws` command to publish everything to our
-# bucket.
-- bash: |
-    set -e
-    source src/ci/shared.sh
-    if [ "$AGENT_OS" = "Linux" ]; then
-        rm -rf obj/build/dist/doc
-        upload_dir=obj/build/dist
-    else
-        rm -rf build/dist/doc
-        upload_dir=build/dist
-    fi
-    ls -la $upload_dir
-    deploy_dir=rustc-builds
-    if [ "$DEPLOY_ALT" == "1" ]; then
-        deploy_dir=rustc-builds-alt
-    fi
-    retry aws s3 cp --no-progress --recursive --acl public-read ./$upload_dir s3://$DEPLOY_BUCKET/$deploy_dir/$BUILD_SOURCEVERSION
+- bash: src/ci/scripts/upload-artifacts.sh
   env:
     AWS_ACCESS_KEY_ID: $(UPLOAD_AWS_ACCESS_KEY_ID)
     AWS_SECRET_ACCESS_KEY: $(UPLOAD_AWS_SECRET_ACCESS_KEY)
-  condition: and(succeeded(), not(variables.SKIP_JOB), or(eq(variables.DEPLOY, '1'), eq(variables.DEPLOY_ALT, '1')))
   displayName: Upload artifacts
-
-# Upload CPU usage statistics that we've been gathering this whole time. Always
-# execute this step in case we want to inspect failed builds, but don't let
-# errors here ever fail the build since this is just informational.
-- bash: aws s3 cp --acl public-read cpu-usage.csv s3://$DEPLOY_BUCKET/rustc-builds/$BUILD_SOURCEVERSION/cpu-$CI_JOB_NAME.csv
-  env:
-    AWS_ACCESS_KEY_ID: $(UPLOAD_AWS_ACCESS_KEY_ID)
-    AWS_SECRET_ACCESS_KEY: $(UPLOAD_AWS_SECRET_ACCESS_KEY)
-  condition: variables['UPLOAD_AWS_SECRET_ACCESS_KEY']
-  continueOnError: true
-  displayName: Upload CPU usage statistics
+  # Adding a condition on DEPLOY=1 or DEPLOY_ALT=1 is not needed as all deploy
+  # builders *should* have the AWS credentials available. Still, explicitly
+  # adding the condition is helpful as this way CI will not silently skip
+  # deploying artifacts from a dist builder if the variables are misconfigured,
+  # erroring about invalid credentials instead.
+  condition: |
+    and(
+      succeeded(), not(variables.SKIP_JOB),
+      or(
+        variables.UPLOAD_AWS_SECRET_ACCESS_KEY,
+        eq(variables.DEPLOY, '1'), eq(variables.DEPLOY_ALT, '1')
+      )
+    )
diff --git a/src/ci/docker/run.sh b/src/ci/docker/run.sh
index 415d6b63eb8dc..cdafcbadc9ec7 100755
--- a/src/ci/docker/run.sh
+++ b/src/ci/docker/run.sh
@@ -106,6 +106,7 @@ fi
 mkdir -p $HOME/.cargo
 mkdir -p $objdir/tmp
 mkdir -p $objdir/cores
+mkdir -p /tmp/toolstate
 
 args=
 if [ "$SCCACHE_BUCKET" != "" ]; then
@@ -156,6 +157,7 @@ else
   args="$args --volume $objdir:/checkout/obj"
   args="$args --volume $HOME/.cargo:/cargo"
   args="$args --volume $HOME/rustsrc:$HOME/rustsrc"
+  args="$args --volume /tmp/toolstate:/tmp/toolstate"
   args="$args --env LOCAL_USER_ID=`id -u`"
 fi
 
diff --git a/src/ci/docker/x86_64-gnu-tools/Dockerfile b/src/ci/docker/x86_64-gnu-tools/Dockerfile
index 8035195c6ed0a..7687a6ca23e18 100644
--- a/src/ci/docker/x86_64-gnu-tools/Dockerfile
+++ b/src/ci/docker/x86_64-gnu-tools/Dockerfile
@@ -26,5 +26,5 @@ ENV CHECK_LINKS 1
 
 ENV RUST_CONFIGURE_ARGS \
   --build=x86_64-unknown-linux-gnu \
-  --save-toolstates=/tmp/toolstates.json
-ENV SCRIPT /tmp/checktools.sh ../x.py /tmp/toolstates.json linux
+  --save-toolstates=/tmp/toolstate/toolstates.json
+ENV SCRIPT /tmp/checktools.sh ../x.py /tmp/toolstate/toolstates.json linux
diff --git a/src/ci/docker/x86_64-gnu-tools/checktools.sh b/src/ci/docker/x86_64-gnu-tools/checktools.sh
index 4243effdf9b4b..ebb8c0bda53ee 100755
--- a/src/ci/docker/x86_64-gnu-tools/checktools.sh
+++ b/src/ci/docker/x86_64-gnu-tools/checktools.sh
@@ -3,7 +3,7 @@
 set -eu
 
 X_PY="$1"
-TOOLSTATE_FILE="$(realpath $2)"
+TOOLSTATE_FILE="$(realpath -m $2)"
 OS="$3"
 COMMIT="$(git rev-parse HEAD)"
 CHANGED_FILES="$(git diff --name-status HEAD HEAD^)"
@@ -13,6 +13,7 @@ SIX_WEEK_CYCLE="$(( ($(date +%s) / 86400 - 20) % 42 ))"
 #   The Wednesday after this has value 0.
 #   We track this value to prevent regressing tools in the last week of the 6-week cycle.
 
+mkdir -p "$(dirname $TOOLSTATE_FILE)"
 touch "$TOOLSTATE_FILE"
 
 # Try to test all the tools and store the build/test success in the TOOLSTATE_FILE
diff --git a/src/ci/scripts/upload-artifacts.sh b/src/ci/scripts/upload-artifacts.sh
new file mode 100755
index 0000000000000..312ec9d805012
--- /dev/null
+++ b/src/ci/scripts/upload-artifacts.sh
@@ -0,0 +1,41 @@
+#!/bin/bash
+# Upload all the artifacts to our S3 bucket. All the files inside ${upload_dir}
+# will be uploaded to the deploy bucket and eventually signed and released in
+# static.rust-lang.org.
+
+set -euo pipefail
+IFS=$'\n\t'
+
+source "$(cd "$(dirname "$0")" && pwd)/../shared.sh"
+
+upload_dir="$(mktemp -d)"
+
+# Release tarballs produced by a dist builder.
+if [[ "${DEPLOY-0}" -eq "1" ]] || [[ "${DEPLOY_ALT-0}" -eq "1" ]]; then
+    dist_dir=build/dist
+    if isLinux; then
+        dist_dir=obj/build/dist
+    fi
+    rm -rf "${dist_dir}/doc"
+    cp -r "${dist_dir}"/* "${upload_dir}"
+fi
+
+# CPU usage statistics.
+cp cpu-usage.csv "${upload_dir}/cpu-${CI_JOB_NAME}.csv"
+
+# Toolstate data.
+if [[ -n "${DEPLOY_TOOLSTATES_JSON+x}" ]]; then
+    cp /tmp/toolstate/toolstates.json "${upload_dir}/${DEPLOY_TOOLSTATES_JSON}"
+fi
+
+echo "Files that will be uploaded:"
+ls -lah "${upload_dir}"
+echo
+
+deploy_dir="rustc-builds"
+if [[ "${DEPLOY_ALT-0}" -eq "1" ]]; then
+    deploy_dir="rustc-builds-alt"
+fi
+deploy_url="s3://${DEPLOY_BUCKET}/${deploy_dir}/$(ciCommit)"
+
+retry aws s3 cp --no-progress --recursive --acl public-read "${upload_dir}" "${deploy_url}"
diff --git a/src/ci/shared.sh b/src/ci/shared.sh
index 37e45b5639dc9..718a5379ae558 100644
--- a/src/ci/shared.sh
+++ b/src/ci/shared.sh
@@ -46,6 +46,10 @@ function getCIBranch {
   echo "$BUILD_SOURCEBRANCHNAME"
 }
 
+function ciCommit {
+  echo "${BUILD_SOURCEVERSION}"
+}
+
 function ciCommandAddPath {
     if [[ $# -ne 1 ]]; then
         echo "usage: $0 <path>"