diff --git a/Library/Homebrew/extend/api_hashable.rb b/Library/Homebrew/extend/api_hashable.rb
index e1e4098e9516b..9719568adf21c 100644
--- a/Library/Homebrew/extend/api_hashable.rb
+++ b/Library/Homebrew/extend/api_hashable.rb
@@ -3,6 +3,43 @@
 
 # Used to substitute common paths with generic placeholders when generating JSON for the API.
 module APIHashable
+  extend T::Helpers
+
+  requires_ancestor { Module }
+
+  module CaskURLFallbackExtension
+    extend T::Helpers
+
+    requires_ancestor { Kernel }
+    requires_ancestor { Cask::Cask }
+
+    def url(...)
+      url = super
+
+      # URLs with blocks are lazy-evaluated, so we let's force an evaluation to ensure the URL can be determined
+      begin
+        url.to_s
+      rescue
+        raise unless self.class.generating_hash?
+        raise unless (json_cask = Homebrew::API::Cask.all_casks[token])
+
+        prev_url = json_cask["url"]
+        prev_specs = json_cask["url_specs"] || {}
+        url = Cask::URL.new(prev_url, **prev_specs)
+
+        opoo "Unable to determine URL for #{token}. Falling back to previous value: #{url}"
+      end
+
+      url
+    end
+  end
+
+  def self.extended(base)
+    return if base != Cask::Cask
+
+    base.prepend CaskURLFallbackExtension
+  end
+
   def generating_hash!
     return if generating_hash?