diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5d6ea81e6..2ecbf33d2 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -6,6 +6,7 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
 
 ### Fixed
 
+* Always download the pinned version of pip in pipstrap to address breakages
 * Rename old,default.conf to old-and-default.conf to address commas in filenames
   breaking recent versions of pip.
 * Add VIRTUALENV_NO_DOWNLOAD=1 to all calls to virtualenv to address breakages
diff --git a/letsencrypt-auto-source/letsencrypt-auto b/letsencrypt-auto-source/letsencrypt-auto
index d387f1934..ffa93262d 100755
--- a/letsencrypt-auto-source/letsencrypt-auto
+++ b/letsencrypt-auto-source/letsencrypt-auto
@@ -1398,9 +1398,6 @@ def get_index_base():
 def main():
     pip_version = StrictVersion(check_output(['pip', '--version'])
                                 .decode('utf-8').split()[1])
-    min_pip_version = StrictVersion(PIP_VERSION)
-    if pip_version >= min_pip_version:
-        return 0
     has_pip_cache = pip_version >= StrictVersion('6.0')
     index_base = get_index_base()
     temp = mkdtemp(prefix='pipstrap-')
diff --git a/letsencrypt-auto-source/pieces/pipstrap.py b/letsencrypt-auto-source/pieces/pipstrap.py
index 727040c3c..2b3025776 100755
--- a/letsencrypt-auto-source/pieces/pipstrap.py
+++ b/letsencrypt-auto-source/pieces/pipstrap.py
@@ -148,9 +148,6 @@ def get_index_base():
 def main():
     pip_version = StrictVersion(check_output(['pip', '--version'])
                                 .decode('utf-8').split()[1])
-    min_pip_version = StrictVersion(PIP_VERSION)
-    if pip_version >= min_pip_version:
-        return 0
     has_pip_cache = pip_version >= StrictVersion('6.0')
     index_base = get_index_base()
     temp = mkdtemp(prefix='pipstrap-')