diff --git a/diskimage_builder/elements/simple-init/install.d/simple-init-repo-install/40-glean b/diskimage_builder/elements/simple-init/install.d/simple-init-repo-install/40-glean
index 5a838de7..246d78c6 100755
--- a/diskimage_builder/elements/simple-init/install.d/simple-init-repo-install/40-glean
+++ b/diskimage_builder/elements/simple-init/install.d/simple-init-repo-install/40-glean
@@ -22,6 +22,9 @@ set -eu
 set -o pipefail
 
 python3 -m venv /usr/glean
+# glean requires PBR to install. We explicitly pip install it to avoid
+# SNI problems with pypi.org on older distros.
+/usr/glean/bin/pip install pbr
 /usr/glean/bin/pip install /tmp/glean.git
 
 mkdir -p /usr/local/bin
diff --git a/diskimage_builder/elements/simple-init/install.d/simple-init-source-install/40-glean b/diskimage_builder/elements/simple-init/install.d/simple-init-source-install/40-glean
index 2107a87d..37603ed8 100755
--- a/diskimage_builder/elements/simple-init/install.d/simple-init-source-install/40-glean
+++ b/diskimage_builder/elements/simple-init/install.d/simple-init-source-install/40-glean
@@ -22,6 +22,9 @@ set -eu
 set -o pipefail
 
 python3 -m venv /usr/glean
+# glean requires PBR to install. We explicitly pip install it to avoid
+# SNI problems with pypi.org on older distros.
+/usr/glean/bin/pip install pbr
 /usr/glean/bin/pip install glean
 
 mkdir -p /usr/local/bin