diff --git a/grpc/src/compiler/python_generator.cc b/grpc/src/compiler/python_generator.cc
index 7e50266354e..027c4a46eb5 100644
--- a/grpc/src/compiler/python_generator.cc
+++ b/grpc/src/compiler/python_generator.cc
@@ -130,7 +130,7 @@ class StubGenerator : public BaseGenerator {
                 const Version& version)
       : BaseGenerator(parser, kStubConfig, path, version) {}
 
-  bool Generate() {
+  const char* Generate() {
     Imports imports;
     std::stringstream stub;
     std::string ns_name{};
@@ -150,8 +150,8 @@ class StubGenerator : public BaseGenerator {
   }
 
  private:
-  bool SaveStub(const std::string& filename, const Imports& imports,
-                const std::string& content) {
+  const char* SaveStub(const std::string& filename, const Imports& imports,
+                       const std::string& content) {
     std::stringstream ss;
     ss << "# Generated by the gRPC FlatBuffers compiler. DO NOT EDIT!\n"
        << '\n'
@@ -161,7 +161,8 @@ class StubGenerator : public BaseGenerator {
     ss << content << '\n';
 
     EnsureDirExists(StripFileName(filename));
-    return parser_.opts.file_saver->SaveFile(filename.c_str(), ss.str(), false);
+    return parser_.opts.file_saver->AttemptSave(filename.c_str(), ss.str(),
+                                                false);
   }
 
   void Generate(std::stringstream& ss, const ServiceDef* service,
@@ -246,7 +247,7 @@ class ServiceGenerator : public BaseGenerator {
                    const Version& version)
       : BaseGenerator(parser, kConfig, path, version) {}
 
-  bool Generate() {
+  const char* Generate() {
     Imports imports;
     std::stringstream ss;
 
@@ -282,8 +283,8 @@ class ServiceGenerator : public BaseGenerator {
   }
 
  private:
-  bool SaveService(const std::string& filename, const Imports& imports,
-                   const std::string& content) {
+  const char* SaveService(const std::string& filename, const Imports& imports,
+                          const std::string& content) {
     std::stringstream ss;
     ss << "# Generated by the gRPC FlatBuffers compiler. DO NOT EDIT!\n"
        << '\n';
@@ -291,7 +292,8 @@ class ServiceGenerator : public BaseGenerator {
     ss << content << '\n';
 
     EnsureDirExists(StripFileName(filename));
-    return parser_.opts.file_saver->SaveFile(filename.c_str(), ss.str(), false);
+    return parser_.opts.file_saver->AttemptSave(filename.c_str(), ss.str(),
+                                                false);
   }
 
   void GenerateStub(std::stringstream& ss, const ServiceDef* service,
@@ -395,14 +397,14 @@ class ServiceGenerator : public BaseGenerator {
 };
 }  // namespace
 
-bool Generate(const Parser& parser, const std::string& path,
-              const Version& version) {
+const char* Generate(const Parser& parser, const std::string& path,
+                     const Version& version) {
   ServiceGenerator generator{parser, path, version};
   return generator.Generate();
 }
 
-bool GenerateStub(const Parser& parser, const std::string& path,
-                  const Version& version) {
+const char* GenerateStub(const Parser& parser, const std::string& path,
+                         const Version& version) {
   StubGenerator generator{parser, path, version};
   return generator.Generate();
 }
diff --git a/grpc/src/compiler/python_generator.h b/grpc/src/compiler/python_generator.h
index 5967e1f84c3..d4146be4e91 100644
--- a/grpc/src/compiler/python_generator.h
+++ b/grpc/src/compiler/python_generator.h
@@ -27,11 +27,11 @@
 namespace flatbuffers {
 namespace python {
 namespace grpc {
-bool Generate(const Parser& parser, const std::string& path,
-              const Version& version);
+const char* Generate(const Parser& parser, const std::string& path,
+                     const Version& version);
 
-bool GenerateStub(const Parser& parser, const std::string& path,
-                  const Version& version);
+const char* GenerateStub(const Parser& parser, const std::string& path,
+                         const Version& version);
 }  // namespace grpc
 }  // namespace python
 }  // namespace flatbuffers
diff --git a/include/flatbuffers/code_generators.h b/include/flatbuffers/code_generators.h
index d284ac5a683..0e69eb8f12f 100644
--- a/include/flatbuffers/code_generators.h
+++ b/include/flatbuffers/code_generators.h
@@ -93,6 +93,10 @@ class BaseGenerator {
  public:
   virtual bool generate() = 0;
 
+  // Modern alternative to bool generate() as this provides a way to
+  // return a specific error message in case of an error and nullptr on success.
+  virtual const char* Generate() { return nullptr; }
+
   static std::string NamespaceDir(const Parser& parser, const std::string& path,
                                   const Namespace& ns,
                                   const bool dasherize = false);
diff --git a/include/flatbuffers/file_manager.h b/include/flatbuffers/file_manager.h
index bafe6f29b97..ded50399b57 100644
--- a/include/flatbuffers/file_manager.h
+++ b/include/flatbuffers/file_manager.h
@@ -33,10 +33,18 @@ class FileSaver {
   virtual bool SaveFile(const char* name, const char* buf, size_t len,
                         bool binary) = 0;
 
+  virtual const char* AttemptSave(const char* name, const char* buf, size_t len,
+                                  bool binary) = 0;
+
   bool SaveFile(const char* name, const std::string& buf, bool binary) {
     return SaveFile(name, buf.c_str(), buf.size(), binary);
   }
 
+  const char* AttemptSave(const char* name, const std::string& buf,
+                          bool binary) {
+    return AttemptSave(name, buf.c_str(), buf.size(), binary);
+  }
+
   virtual void Finish() {}
 
  private:
@@ -52,6 +60,9 @@ class RealFileSaver final : public FileSaver {
  public:
   bool SaveFile(const char* name, const char* buf, size_t len,
                 bool binary) final;
+
+  const char* AttemptSave(const char* name, const char* buf, size_t len,
+                          bool binary) final;
 };
 
 class FileNameSaver final : public FileSaver {
@@ -59,6 +70,9 @@ class FileNameSaver final : public FileSaver {
   bool SaveFile(const char* name, const char* buf, size_t len,
                 bool binary) final;
 
+  const char* AttemptSave(const char* name, const char* buf, size_t len,
+                          bool binary) final;
+
   void Finish() final;
 
  private:
diff --git a/include/flatbuffers/idl.h b/include/flatbuffers/idl.h
index 4139529a11a..5426ad39157 100644
--- a/include/flatbuffers/idl.h
+++ b/include/flatbuffers/idl.h
@@ -1303,8 +1303,8 @@ bool GenerateJavaGRPC(const Parser& parser, const std::string& path,
 
 // Generate GRPC Python interfaces.
 // See idl_gen_grpc.cpp.
-bool GeneratePythonGRPC(const Parser& parser, const std::string& path,
-                        const std::string& file_name);
+const char* GeneratePythonGRPC(const Parser& parser, const std::string& path,
+                               const std::string& file_name);
 
 // Generate GRPC Swift interfaces.
 // See idl_gen_grpc.cpp.
diff --git a/src/file_manager.cpp b/src/file_manager.cpp
index 13b1580af04..276c5693014 100644
--- a/src/file_manager.cpp
+++ b/src/file_manager.cpp
@@ -14,12 +14,12 @@
  * limitations under the License.
  */
 
+#include "flatbuffers/file_manager.h"
+
 #include <fstream>
 #include <set>
 #include <string>
 
-#include "flatbuffers/file_manager.h"
-
 namespace flatbuffers {
 
 bool RealFileSaver::SaveFile(const char* name, const char* buf, size_t len,
@@ -30,4 +30,13 @@ bool RealFileSaver::SaveFile(const char* name, const char* buf, size_t len,
   return !ofs.bad();
 }
 
+const char* RealFileSaver::AttemptSave(const char* name, const char* buf,
+                                       size_t len, bool binary) {
+  if (!SaveFile(name, buf, len, binary)) {
+    static std::string error_msg;
+    error_msg = "Could not save file " + std::string(name ? name : "unknown");
+    return error_msg.c_str();
+  }
+  return nullptr;
+}
 }  // namespace flatbuffers
diff --git a/src/file_name_manager.cpp b/src/file_name_manager.cpp
index aad63de8c6b..a2d31a5133f 100644
--- a/src/file_name_manager.cpp
+++ b/src/file_name_manager.cpp
@@ -33,6 +33,12 @@ bool FileNameSaver::SaveFile(const char* name, const char* buf, size_t len,
   return true;
 }
 
+const char* FileNameSaver::AttemptSave(const char* name, const char* buf,
+                                       size_t len, bool binary) {
+  return SaveFile(name, buf, len, binary) ? nullptr
+                                          : "Printing filename failed";
+}
+
 void FileNameSaver::Finish() {
   for (const auto& file_name : file_names_) {
     // Just print the file names to standard output.
diff --git a/src/idl_gen_grpc.cpp b/src/idl_gen_grpc.cpp
index 476fa5ffe02..959e0729836 100644
--- a/src/idl_gen_grpc.cpp
+++ b/src/idl_gen_grpc.cpp
@@ -440,25 +440,26 @@ bool GenerateJavaGRPC(const Parser& parser, const std::string& path,
   return JavaGRPCGenerator(parser, path, file_name).generate();
 }
 
-bool GeneratePythonGRPC(const Parser& parser, const std::string& path,
-                        const std::string& /*file_name*/) {
+const char* GeneratePythonGRPC(const Parser& parser, const std::string& path,
+                               const std::string& /*file_name*/) {
   int nservices = 0;
   for (auto it = parser.services_.vec.begin(); it != parser.services_.vec.end();
        ++it) {
     if (!(*it)->generated) nservices++;
   }
-  if (!nservices) return true;
+  if (!nservices) return nullptr;
 
   flatbuffers::python::Version version{parser.opts.python_version};
-  if (!version.IsValid()) return false;
+  if (!version.IsValid()) return "The provided Python version is not valid";
+
+  auto error = flatbuffers::python::grpc::Generate(parser, path, version);
+  if (error) return error;
 
-  if (!flatbuffers::python::grpc::Generate(parser, path, version)) {
-    return false;
-  }
   if (parser.opts.python_typing) {
-    return flatbuffers::python::grpc::GenerateStub(parser, path, version);
+    auto error = flatbuffers::python::grpc::GenerateStub(parser, path, version);
+    if (error) return error;
   }
-  return true;
+  return nullptr;
 }
 
 class SwiftGRPCGenerator : public flatbuffers::BaseGenerator {
diff --git a/src/idl_gen_python.cpp b/src/idl_gen_python.cpp
index 314c3c2d855..5be928e869a 100644
--- a/src/idl_gen_python.cpp
+++ b/src/idl_gen_python.cpp
@@ -57,7 +57,7 @@ class PythonStubGenerator {
                Keywords(version)},
         version_(version) {}
 
-  bool Generate() {
+  const char* Generate() {
     if (parser_.opts.one_file) {
       Imports imports;
       std::stringstream stub;
@@ -91,7 +91,8 @@ class PythonStubGenerator {
 
       std::string filename = namer_.Directories(*def->defined_namespace) +
                              namer_.File(*def, SkipFile::Suffix);
-      if (!SaveFile(filename, imports, stub)) return false;
+      auto error = SaveFile(filename, imports, stub);
+      if (error) return error;
     }
 
     for (const StructDef* def : parser_.structs_.vec) {
@@ -105,22 +106,24 @@ class PythonStubGenerator {
 
       std::string filename = namer_.Directories(*def->defined_namespace) +
                              namer_.File(*def, SkipFile::Suffix);
-      if (!SaveFile(filename, imports, stub)) return false;
+      auto error = SaveFile(filename, imports, stub);
+      if (error) return error;
     }
 
-    return true;
+    return nullptr;
   }
 
  private:
-  bool SaveFile(const std::string& filename, const Imports& imports,
-                const std::stringstream& content) {
+  const char* SaveFile(const std::string& filename, const Imports& imports,
+                       const std::stringstream& content) {
     std::stringstream ss;
     GenerateImports(ss, imports);
     ss << '\n';
     ss << content.str() << '\n';
 
     EnsureDirExists(StripFileName(filename));
-    return parser_.opts.file_saver->SaveFile(filename.c_str(), ss.str(), false);
+    return parser_.opts.file_saver->AttemptSave(filename.c_str(), ss.str(),
+                                                false);
   }
 
   static void DeclareUOffset(std::stringstream& stub, Imports* imports) {
@@ -2758,11 +2761,15 @@ class PythonGenerator : public BaseGenerator {
     EndBuilderBody(code_ptr);
   }
 
-  bool generate() {
+  bool generate() { return false; }
+
+  const char* Generate() {
     std::string one_file_code;
     ImportMap one_file_imports;
-    if (!generateEnums(&one_file_code)) return false;
-    if (!generateStructs(&one_file_code, one_file_imports)) return false;
+    auto error = generateEnums(&one_file_code);
+    if (error) return error;
+    error = generateStructs(&one_file_code, one_file_imports);
+    if (error) return error;
 
     if (parser_.opts.one_file) {
       const std::string mod = file_name_ + parser_.opts.filename_suffix;
@@ -2772,11 +2779,11 @@ class PythonGenerator : public BaseGenerator {
                       one_file_imports, mod, true);
     }
 
-    return true;
+    return nullptr;
   }
 
  private:
-  bool generateEnums(std::string* one_file_code) const {
+  const char* generateEnums(std::string* one_file_code) const {
     for (auto it = parser_.enums_.vec.begin(); it != parser_.enums_.vec.end();
          ++it) {
       auto& enum_def = **it;
@@ -2793,17 +2800,18 @@ class PythonGenerator : public BaseGenerator {
         const std::string mod =
             namer_.File(enum_def, SkipFile::SuffixAndExtension);
 
-        if (!SaveType(namer_.File(enum_def, SkipFile::Suffix),
-                      *enum_def.defined_namespace, enumcode, imports, mod,
-                      false))
-          return false;
+        auto error = SaveType(namer_.File(enum_def, SkipFile::Suffix),
+                              *enum_def.defined_namespace, enumcode, imports,
+                              mod, false);
+        printf("generateEnums: %s", error);
+        if (error) return error;
       }
     }
-    return true;
+    return nullptr;
   }
 
-  bool generateStructs(std::string* one_file_code,
-                       ImportMap& one_file_imports) const {
+  const char* generateStructs(std::string* one_file_code,
+                              ImportMap& one_file_imports) const {
     for (auto it = parser_.structs_.vec.begin();
          it != parser_.structs_.vec.end(); ++it) {
       auto& struct_def = **it;
@@ -2825,13 +2833,13 @@ class PythonGenerator : public BaseGenerator {
       } else {
         const std::string mod =
             namer_.File(struct_def, SkipFile::SuffixAndExtension);
-        if (!SaveType(namer_.File(struct_def, SkipFile::Suffix),
-                      *struct_def.defined_namespace, declcode, imports, mod,
-                      true))
-          return false;
+        auto error = SaveType(namer_.File(struct_def, SkipFile::Suffix),
+                              *struct_def.defined_namespace, declcode, imports,
+                              mod, true);
+        if (error) return error;
       }
     }
-    return true;
+    return nullptr;
   }
 
   // Begin by declaring namespace and imports.
@@ -2871,10 +2879,10 @@ class PythonGenerator : public BaseGenerator {
   }
 
   // Save out the generated code for a Python Table type.
-  bool SaveType(const std::string& defname, const Namespace& ns,
-                const std::string& classcode, const ImportMap& imports,
-                const std::string& mod, bool needs_imports) const {
-    if (classcode.empty()) return true;
+  const char* SaveType(const std::string& defname, const Namespace& ns,
+                       const std::string& classcode, const ImportMap& imports,
+                       const std::string& mod, bool needs_imports) const {
+    if (classcode.empty()) return nullptr;
 
     std::string code = "";
     BeginFile(LastNamespacePart(ns), needs_imports, &code, mod, imports);
@@ -2885,15 +2893,15 @@ class PythonGenerator : public BaseGenerator {
     EnsureDirExists(directories);
 
     for (size_t i = directories.find(kPathSeparator, path_.size());
-         i != std::string::npos;
-         i = directories.find(kPathSeparator, i + 1)) {
+         i != std::string::npos; i = directories.find(kPathSeparator, i + 1)) {
       const std::string init_py =
           directories.substr(0, i) + kPathSeparator + "__init__.py";
-      parser_.opts.file_saver->SaveFile(init_py.c_str(), "", false);
+      parser_.opts.file_saver->AttemptSave(init_py.c_str(), "",
+                                           false);  // todo return on error
     }
 
     const std::string filename = directories + defname;
-    return parser_.opts.file_saver->SaveFile(filename.c_str(), code, false);
+    return parser_.opts.file_saver->AttemptSave(filename.c_str(), code, false);
   }
 
  private:
@@ -2904,16 +2912,18 @@ class PythonGenerator : public BaseGenerator {
 }  // namespace python
 
 static const char* GeneratePython(const Parser& parser, const std::string& path,
-                           const std::string& file_name) {
+                                  const std::string& file_name) {
   python::Version version{parser.opts.python_version};
   if (!version.IsValid()) return "The provided Python version is not valid";
 
   python::PythonGenerator generator(parser, path, file_name, version);
-  if (!generator.generate()) return "could not generate Python code";
+  auto error = generator.Generate();
+  if (error) return error;
 
   if (parser.opts.python_typing) {
     python::PythonStubGenerator stub_generator(parser, path, version);
-    if (!stub_generator.Generate()) return "could not generate Python type stubs";
+    auto error = stub_generator.Generate();
+    if (error) return error;
   }
   return nullptr;
 }
@@ -2948,7 +2958,9 @@ class PythonCodeGenerator : public CodeGenerator {
 
   Status GenerateGrpcCode(const Parser& parser, const std::string& path,
                           const std::string& filename) override {
-    if (!GeneratePythonGRPC(parser, path, filename)) { // TODO add status GeneratePythonGRPC
+    auto err = GeneratePythonGRPC(parser, path, filename);
+    if (err) {
+      status_detail = " " + std::string(err);
       return Status::ERROR;
     }
     return Status::OK;