diff --git a/Library/Homebrew/dev-cmd/bottle.rb b/Library/Homebrew/dev-cmd/bottle.rb
index 87c7311e65..86cfc8188f 100644
--- a/Library/Homebrew/dev-cmd/bottle.rb
+++ b/Library/Homebrew/dev-cmd/bottle.rb
@@ -334,9 +334,8 @@ module Homebrew
     else
       ohai "Determining #{f.full_name} bottle rebuild..."
       versions = FormulaVersions.new(f)
-      rebuilds = versions.bottle_version_map("origin/master")[f.pkg_version]
-      rebuilds.pop if rebuilds.last.to_i.positive?
-      rebuilds.empty? ? 0 : rebuilds.max.to_i + 1
+      rebuilds = versions.most_recent_rebuild_for_pkg_version("origin/master", f.pkg_version)
+      rebuilds ? rebuilds.to_i + 1 : 0
     end
 
     filename = Bottle::Filename.create(f, bottle_tag.to_sym, rebuild)
diff --git a/Library/Homebrew/formula_versions.rb b/Library/Homebrew/formula_versions.rb
index 0701d643bd..d98830b342 100644
--- a/Library/Homebrew/formula_versions.rb
+++ b/Library/Homebrew/formula_versions.rb
@@ -30,7 +30,8 @@ class FormulaVersions
 
   def rev_list(branch)
     repository.cd do
-      Utils.popen_read("git", "rev-list", "--abbrev-commit", "--remove-empty", branch, "--", entry_name) do |io|
+      Utils.popen_read("git", "rev-list", "--abbrev-commit", "--remove-empty", "--first-parent", branch, "--",
+                       entry_name) do |io|
         yield io.readline.chomp until io.eof?
       end
     end
@@ -57,21 +58,21 @@ class FormulaVersions
     Homebrew.raise_deprecation_exceptions = false
   end
 
-  def bottle_version_map(branch)
-    map = Hash.new { |h, k| h[k] = [] }
-
-    versions_seen = 0
+  def most_recent_rebuild_for_pkg_version(branch, pkg_version)
     rev_list(branch) do |rev|
       formula_at_revision(rev) do |f|
+        odebug "Considering #{rev}. #{f.pkg_version} (rebuild: #{f.bottle_specification.rebuild}"
         bottle = f.bottle_specification
-        map[f.pkg_version] << bottle.rebuild unless bottle.checksums.empty?
-        versions_seen = (map.keys + [f.pkg_version]).uniq.length
+        # If the version is older than the one we want, we've gone too far
+        return if f.pkg_version < pkg_version
+
+        # If this revision has a rebuild number, we are done!
+        return bottle.rebuild if f.pkg_version == pkg_version && !bottle.checksums.empty?
       end
-      return map if versions_seen > MAX_VERSIONS_DEPTH
     rescue MacOSVersionError => e
       odebug "#{e} in #{name} at revision #{rev}"
       break
     end
-    map
+    nil
   end
 end