diff --git a/jenkins/scripts/pypi-tarball-upload.sh b/jenkins/scripts/pypi-tarball-upload.sh
index ac482ee876..cbcfc232cb 100755
--- a/jenkins/scripts/pypi-tarball-upload.sh
+++ b/jenkins/scripts/pypi-tarball-upload.sh
@@ -34,6 +34,21 @@ curl --fail -o $FILENAME http://$TARBALL_SITE/$PROJECT/$FILENAME
 file -b $FILENAME | grep gzip
 
 # Uploads may claim to fail but actually succeed so we check if we
-# can download after upload to determine success.
-twine upload -r pypi $FILENAME || true
-curl --head --silent --fail "https://pypi.python.org/simple/$PROJECT/$FILENAME" >/dev/null 2>&1
+# can download after upload to determine success. They can also fail
+# intermittently, so retrying in a delayed loop helps improve
+# robustness.
+TRY=0
+RETVAL=255
+set +e
+while [[ $TRY -lt 3 ]] && [[ $RETVAL -ne 0 ]]; do
+    twine upload -r pypi $FILENAME
+    curl --head --silent --fail \
+        "https://pypi.python.org/simple/$PROJECT/$FILENAME" >/dev/null 2>&1
+    RETVAL=$?
+    (( TRY++ ))
+    if [[ $TRY -lt 3 ]] && [[ $RETVAL -ne 0 ]]; then
+        echo "Upload failed, retrying in $TRY seconds." >&2
+        sleep $TRY
+    fi
+done
+exit $RETVAL
diff --git a/jenkins/scripts/pypi-wheel-upload.sh b/jenkins/scripts/pypi-wheel-upload.sh
index bf1bbeb11a..572e9d9229 100755
--- a/jenkins/scripts/pypi-wheel-upload.sh
+++ b/jenkins/scripts/pypi-wheel-upload.sh
@@ -36,6 +36,21 @@ curl --fail -o $FILENAME http://$TARBALL_SITE/$PROJECT/$FILENAME
 file -b $FILENAME | grep -i zip
 
 # Uploads may claim to fail but actually succeed so we check if we
-# can download after upload to determine success.
-twine upload -r pypi $FILENAME || true
-curl --head --silent --fail "https://pypi.python.org/simple/$PROJECT/$FILENAME" >/dev/null 2>&1
+# can download after upload to determine success. They can also fail
+# intermittently, so retrying in a delayed loop helps improve
+# robustness.
+TRY=0
+RETVAL=255
+set +e
+while [[ $TRY -lt 3 ]] && [[ $RETVAL -ne 0 ]]; do
+    twine upload -r pypi $FILENAME
+    curl --head --silent --fail \
+        "https://pypi.python.org/simple/$PROJECT/$FILENAME" >/dev/null 2>&1
+    RETVAL=$?
+    (( TRY++ ))
+    if [[ $TRY -lt 3 ]] && [[ $RETVAL -ne 0 ]]; then
+        echo "Upload failed, retrying in $TRY seconds." >&2
+        sleep $TRY
+    fi
+done
+exit $RETVAL