diff --git a/bumpversion/utils.py b/bumpversion/utils.py
index f872f230..787beffb 100644
--- a/bumpversion/utils.py
+++ b/bumpversion/utils.py
@@ -51,17 +51,11 @@ def should_contain_version(self, version, context):
         if self.contains(search_expression):
             return
 
-        # the `search` pattern did not match, but the original supplied
-        # version number (representing the same version part values) might
-        # match instead.
-
-        # check whether `search` isn't customized, i.e. should match only
-        # very specific parts of the file
-        search_pattern_is_default = self._versionconfig.search == "{current_version}"
-
-        if search_pattern_is_default and self.contains(version.original):
-            # original version is present and we're not looking for something
-            # more specific -> this is accepted as a match
+        # try original version to construct search_expression
+        search_expression = self._versionconfig.search.format(
+            current_version=version.original
+        )
+        if self.contains(search_expression):
             return
 
         # version not found
@@ -118,8 +112,11 @@ def replace(self, current_version, new_version, context, dry_run):
 
         if file_content_before == file_content_after:
             # TODO expose this to be configurable
+            search_for_original_formatted = self._versionconfig.search.format(
+                current_version=current_version.original
+            )
             file_content_after = file_content_before.replace(
-                current_version.original, replace_with
+                search_for_original_formatted, replace_with
             )
 
         if file_content_before != file_content_after:
diff --git a/tests/test_cli.py b/tests/test_cli.py
index d41942ba..a22f30c7 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -1506,6 +1506,60 @@ def test_no_list_no_stdout(tmpdir, vcs):
     assert out == ""
 
 
+def test_non_default_search_of_omitted_optional_value(tmpdir):
+    tmpdir.join("version.txt").write("v0.0")
+    tmpdir.chdir()
+
+    tmpdir.join(".bumpversion.cfg").write(dedent(r"""
+                [bumpversion]
+                current_version = 0.0
+                parse = (?P<major>\d+)\.(?P<minor>\d+)(\-?(?P<release>[a-z]+))?
+                serialize =
+                  {major}.{minor}-{release}
+                  {major}.{minor}
+
+                [bumpversion:part:release]
+                optional_value = prod
+                values =
+                  dev
+                  prod
+                [bumpversion:file:version.txt]
+                search = v{current_version}
+                replace = {new_version}
+                """).strip())
+    try:
+        main(['minor'])
+    except exceptions.VersionNotFoundException as e:
+        pytest.fail(
+                str(e) + "\n\t- '0.0' is equivalent to '0.0-prod', so 'v0.0' should be found"
+        )
+
+
+def test_non_default_replace_of_omitted_optional_value(tmpdir):
+    tmpdir.join("version.txt").write("v0.0")
+    tmpdir.chdir()
+
+    tmpdir.join(".bumpversion.cfg").write(dedent(r"""
+                    [bumpversion]
+                    current_version = 0.0
+                    parse = (?P<major>\d+)\.(?P<minor>\d+)(\-?(?P<release>[a-z]+))?
+                    serialize =
+                      {major}.{minor}-{release}
+                      {major}.{minor}
+
+                    [bumpversion:part:release]
+                    optional_value = prod
+                    values =
+                      dev
+                      prod
+                    [bumpversion:file:version.txt]
+                    search = v{current_version}
+                    replace = v{new_version}
+                    """).strip())
+    main(['minor'])
+    assert 'v0.1-dev' == tmpdir.join("version.txt").read()
+
+
 def test_bump_non_numeric_parts(tmpdir):
     tmpdir.join("with_pre_releases.txt").write("1.5.dev")
     tmpdir.chdir()