diff --git a/certbot/CHANGELOG.md b/certbot/CHANGELOG.md
index de6ca2039..f9589d24e 100644
--- a/certbot/CHANGELOG.md
+++ b/certbot/CHANGELOG.md
@@ -11,6 +11,8 @@ Certbot adheres to [Semantic Versioning](https://semver.org/).
 ### Changed
 
 * DNS plugins based on lexicon now require dns-lexicon >= v3.1.0
+* Windows installer now cleans up old Certbot dependency packages
+  before installing the new ones to avoid version conflicts.
 
 ### Fixed
 
diff --git a/windows-installer/assets/template.nsi b/windows-installer/assets/template.nsi
index 566e1b004..5c551729a 100644
--- a/windows-installer/assets/template.nsi
+++ b/windows-installer/assets/template.nsi
@@ -83,6 +83,11 @@ SectionEnd
 [% block sections %]
 
 Section "!${PRODUCT_NAME}" sec_app
+  ; CERTBOT CUSTOM BEGIN
+  ; Try to cleanup Certbot pkg directory to avoid dependencies conflicts
+  RMDir /r "$INSTDIR\pkgs"
+  ; CERTBOT CUSTOM END
+
   SetRegView [[ib.py_bitness]]
   SectionIn RO
   File ${PRODUCT_ICON}