diff --git a/changelog/v1.29.3-patch2/base64url.yaml b/changelog/v1.29.3-patch2/base64url.yaml
new file mode 100644
index 000000000..c6056bd1e
--- /dev/null
+++ b/changelog/v1.29.3-patch2/base64url.yaml
@@ -0,0 +1,7 @@
+changelog:
+- type: FIX
+  issueLink: https://github.com/solo-io/envoy-gloo/issues/329
+  resolvesIssue: false
+  description: >-
+    Fall back to attempting to decode Base64Url if Base64 decoding fails in the Inja transformation
+    base64_decode callback. This can happen especially when attempting to decode JWTs.
diff --git a/source/extensions/filters/http/transformation/inja_transformer.cc b/source/extensions/filters/http/transformation/inja_transformer.cc
index c5022de7e..2d258e5df 100644
--- a/source/extensions/filters/http/transformation/inja_transformer.cc
+++ b/source/extensions/filters/http/transformation/inja_transformer.cc
@@ -10,6 +10,7 @@
 #include "source/common/regex/regex.h"
 #include "source/common/common/utility.h"
 #include "source/common/config/metadata.h"
+#include "source/common/common/empty_string.h"
 
 #include "source/extensions/filters/http/solo_well_known_names.h"
 
@@ -238,9 +239,15 @@ TransformerInstance::TransformerInstance(ThreadLocal::Slot &tls, Envoy::Random::
   env_.add_callback("base64_encode", 1, [this](Arguments &args) {
     return base64_encode_callback(args);
   });
+  env_.add_callback("base64url_encode", 1, [this](Arguments &args) {
+    return base64url_encode_callback(args);
+  });
   env_.add_callback("base64_decode", 1, [this](Arguments &args) {
     return base64_decode_callback(args);
   });
+  env_.add_callback("base64url_decode", 1, [this](Arguments &args) {
+    return base64url_decode_callback(args);
+  });
   // substring can be called with either two or three arguments --
   // the first argument is the string to be modified, the second is the start position
   // of the substring, and the optional third argument is the length of the substring.
@@ -388,11 +395,21 @@ json TransformerInstance::base64_encode_callback(const inja::Arguments &args) co
   return Base64::encode(input.c_str(), input.length());
 }
 
+json TransformerInstance::base64url_encode_callback(const inja::Arguments &args) const {
+  const std::string &input = args.at(0)->get_ref<const std::string &>();
+  return Base64Url::encode(input.c_str(), input.length());
+}
+
 json TransformerInstance::base64_decode_callback(const inja::Arguments &args) const {
   const std::string &input = args.at(0)->get_ref<const std::string &>();
   return Base64::decode(input);
 }
 
+json TransformerInstance::base64url_decode_callback(const inja::Arguments &args) const {
+  const std::string &input = args.at(0)->get_ref<const std::string &>();
+  return Base64Url::decode(input);
+}
+
 // return a substring of the input string, starting at the start position
 // and extending for length characters. If length is not provided, the
 // substring will extend to the end of the string.
diff --git a/source/extensions/filters/http/transformation/inja_transformer.h b/source/extensions/filters/http/transformation/inja_transformer.h
index 97861da47..829978780 100644
--- a/source/extensions/filters/http/transformation/inja_transformer.h
+++ b/source/extensions/filters/http/transformation/inja_transformer.h
@@ -66,7 +66,9 @@ class TransformerInstance {
   nlohmann::json env(const inja::Arguments &args) const;
   nlohmann::json cluster_metadata_callback(const inja::Arguments &args) const;
   nlohmann::json base64_encode_callback(const inja::Arguments &args) const;
+  nlohmann::json base64url_encode_callback(const inja::Arguments &args) const;
   nlohmann::json base64_decode_callback(const inja::Arguments &args) const;
+  nlohmann::json base64url_decode_callback(const inja::Arguments &args) const;
   nlohmann::json substring_callback(const inja::Arguments &args) const;
   nlohmann::json replace_with_random_callback(const inja::Arguments &args);
   std::string& random_for_pattern(const std::string& pattern);
diff --git a/test/extensions/filters/http/transformation/inja_transformer_test.cc b/test/extensions/filters/http/transformation/inja_transformer_test.cc
index f0fd7e6d0..3b57c9f9b 100644
--- a/test/extensions/filters/http/transformation/inja_transformer_test.cc
+++ b/test/extensions/filters/http/transformation/inja_transformer_test.cc
@@ -882,6 +882,28 @@ TEST_F(InjaTransformerTest, Base64DecodeTestString) {
   EXPECT_EQ(body.toString(), test_string);
 }
 
+TEST_F(InjaTransformerTest, Base64UrlDecodeJWT) {
+  Http::TestRequestHeaderMapImpl headers{{":method", "GET"}, {":path", "/foo"}};
+  TransformationTemplate transformation;
+
+  // Test string that produced the base64url underscore
+  auto expect_string = "aaoð";
+  // JWT with an underscore which is an invalid base64 character
+  auto encoded_string = "eyJzdWIiOiJhYW_DsCJ9";
+
+  auto formatted_string = fmt::format("{{{{base64url_decode(\"{}\")}}}}", encoded_string);
+
+  transformation.mutable_body()->set_text(formatted_string);
+
+  InjaTransformer transformer(transformation, rng_, google::protobuf::BoolValue(), tls_);
+
+  NiceMock<Http::MockStreamDecoderFilterCallbacks> callbacks;
+
+  Buffer::OwnedImpl body("");
+  transformer.transform(headers, &headers, body, callbacks);
+  EXPECT_NE(std::string::npos, body.toString().find(expect_string));
+}
+
 TEST_F(InjaTransformerTest, Base64Composed) {
   Http::TestRequestHeaderMapImpl headers{{":method", "GET"}, {":path", "/foo"}};
   TransformationTemplate transformation;