diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index 257e0501..bfe65d8a 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -31,6 +31,12 @@ jobs:
   # Installing six is a workaround for pip dependency resolution: six is already
   # installed as system package with a version below the required one.
   # Explicitly installing six through pip gets us a supported version.
+  #
+  # Updating pip and setuptools is required to have these tools properly parse
+  # Python-version metadata, which some packages uses to specify that an older
+  # version of a package must be used for a certain Python version. If that
+  # information is not read, pip installs the latest version, which then fails
+  # to run.
   - bash: |
       sudo apt-get install -y \
           python3 \
@@ -47,7 +53,8 @@ jobs:
           curl \
           libelf-dev \
           clang-format \
-        && sudo pip3 install -U six fusesoc
+        && sudo pip3 install -U setuptools pip six \
+        && sudo pip3 install -U fusesoc
     displayName: Install dependencies
 
   - bash: |