diff --git a/Vagrantfile b/Vagrantfile
index 8cde07311..662eccf18 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -108,6 +108,9 @@ $frontend = <<-SHELL
   # Install learn deps
   python3 -m venv /vagrant/venv
   source /vagrant/venv/bin/activate
+  # Pinned like CI's setup-python pip-version input: pip itself is the one
+  # tool that resolves the pinned packages below, so it needs a pin too.
+  pip3 install --upgrade pip==26.2.1
   pip3 install -r /vagrant/frontend/requirements_frozen.txt
   pip3 install -e /vagrant/frontend/python/rst_code_example_pipeline
 
@@ -275,6 +278,9 @@ $epub = <<-SHELL
   # Install learn deps
   python3 -m venv /vagrant/venv
   source /vagrant/venv/bin/activate
+  # Pinned like CI's setup-python pip-version input: pip itself is the one
+  # tool that resolves the pinned packages below, so it needs a pin too.
+  pip3 install --upgrade pip==26.2.1
   pip3 install -r /vagrant/frontend/requirements_frozen.txt
   pip3 install -e /vagrant/frontend/python/rst_code_example_pipeline