diff --git a/src/app/core/core_library.cmake b/src/app/core/core_library.cmake
index 96e54129..1be51b74 100644
--- a/src/app/core/core_library.cmake
+++ b/src/app/core/core_library.cmake
@@ -151,6 +151,11 @@ if(YAZE_WITH_GRPC)
     libprotobuf
   )
   
+  # On Windows, force whole-archive linking for protobuf to ensure all symbols are included
+  if(MSVC)
+    target_link_options(yaze_core_lib PUBLIC /WHOLEARCHIVE:libprotobuf)
+  endif()
+  
   message(STATUS "  - gRPC test harness + ROM service enabled")
 endif()
 
diff --git a/src/app/net/net_library.cmake b/src/app/net/net_library.cmake
index 4f37d610..a491afbd 100644
--- a/src/app/net/net_library.cmake
+++ b/src/app/net/net_library.cmake
@@ -52,14 +52,21 @@ if(YAZE_WITH_JSON)
   find_package(Threads REQUIRED)
   target_link_libraries(yaze_net PUBLIC Threads::Threads)
   
-  # Add OpenSSL for HTTPS/WSS support (optional but recommended)
-  find_package(OpenSSL QUIET)
-  if(OpenSSL_FOUND)
-    target_link_libraries(yaze_net PUBLIC OpenSSL::SSL OpenSSL::Crypto)
-    target_compile_definitions(yaze_net PUBLIC CPPHTTPLIB_OPENSSL_SUPPORT)
-    message(STATUS "  - WebSocket with SSL/TLS support enabled")
+  # Only link OpenSSL if gRPC is NOT enabled (to avoid duplicate symbol errors)
+  # When gRPC is enabled, it brings its own OpenSSL which we'll use instead
+  if(NOT YAZE_WITH_GRPC)
+    find_package(OpenSSL QUIET)
+    if(OpenSSL_FOUND)
+      target_link_libraries(yaze_net PUBLIC OpenSSL::SSL OpenSSL::Crypto)
+      target_compile_definitions(yaze_net PUBLIC CPPHTTPLIB_OPENSSL_SUPPORT)
+      message(STATUS "  - WebSocket with SSL/TLS support enabled")
+    else()
+      message(STATUS "  - WebSocket without SSL/TLS (OpenSSL not found)")
+    endif()
   else()
-    message(STATUS "  - WebSocket without SSL/TLS (OpenSSL not found)")
+    # When gRPC is enabled, still enable OpenSSL features but use gRPC's OpenSSL
+    target_compile_definitions(yaze_net PUBLIC CPPHTTPLIB_OPENSSL_SUPPORT)
+    message(STATUS "  - WebSocket with SSL/TLS support enabled via gRPC's OpenSSL")
   endif()
   
   # Windows-specific socket library
@@ -79,6 +86,11 @@ if(YAZE_WITH_GRPC)
     libprotobuf
   )
   
+  # On Windows, force whole-archive linking for protobuf to ensure all symbols are included
+  if(MSVC)
+    target_link_options(yaze_net PUBLIC /WHOLEARCHIVE:libprotobuf)
+  endif()
+  
   message(STATUS "  - gRPC ROM service enabled")
 endif()
 
diff --git a/src/cli/agent.cmake b/src/cli/agent.cmake
index bbec6ca8..665667c4 100644
--- a/src/cli/agent.cmake
+++ b/src/cli/agent.cmake
@@ -110,20 +110,32 @@ if(YAZE_WITH_JSON)
   target_link_libraries(yaze_agent PUBLIC nlohmann_json::nlohmann_json)
   target_compile_definitions(yaze_agent PUBLIC YAZE_WITH_JSON)
 
-  find_package(OpenSSL)
-  if(OpenSSL_FOUND)
-    target_compile_definitions(yaze_agent PUBLIC CPPHTTPLIB_OPENSSL_SUPPORT)
-    target_link_libraries(yaze_agent PUBLIC OpenSSL::SSL OpenSSL::Crypto)
+  # Only link OpenSSL if gRPC is NOT enabled (to avoid duplicate symbol errors)
+  # When gRPC is enabled, it brings its own OpenSSL which we'll use instead
+  if(NOT YAZE_WITH_GRPC)
+    find_package(OpenSSL)
+    if(OpenSSL_FOUND)
+      target_compile_definitions(yaze_agent PUBLIC CPPHTTPLIB_OPENSSL_SUPPORT)
+      target_link_libraries(yaze_agent PUBLIC OpenSSL::SSL OpenSSL::Crypto)
 
+      if(APPLE)
+        target_compile_definitions(yaze_agent PUBLIC CPPHTTPLIB_USE_CERTS_FROM_MACOSX_KEYCHAIN)
+        target_link_libraries(yaze_agent PUBLIC "-framework CoreFoundation" "-framework Security")
+      endif()
+
+      message(STATUS "✓ SSL/HTTPS support enabled for yaze_agent (Gemini + HTTPS)")
+    else()
+      message(WARNING "OpenSSL not found - Gemini HTTPS features disabled (Ollama still works)")
+      message(STATUS "  Install OpenSSL to enable Gemini: brew install openssl (macOS) or apt-get install libssl-dev (Linux)")
+    endif()
+  else()
+    # When gRPC is enabled, still enable OpenSSL features but use gRPC's OpenSSL
+    target_compile_definitions(yaze_agent PUBLIC CPPHTTPLIB_OPENSSL_SUPPORT)
     if(APPLE)
       target_compile_definitions(yaze_agent PUBLIC CPPHTTPLIB_USE_CERTS_FROM_MACOSX_KEYCHAIN)
       target_link_libraries(yaze_agent PUBLIC "-framework CoreFoundation" "-framework Security")
     endif()
-
-    message(STATUS "✓ SSL/HTTPS support enabled for yaze_agent (Gemini + HTTPS)")
-  else()
-    message(WARNING "OpenSSL not found - Gemini HTTPS features disabled (Ollama still works)")
-    message(STATUS "  Install OpenSSL to enable Gemini: brew install openssl (macOS) or apt-get install libssl-dev (Linux)")
+    message(STATUS "✓ SSL/HTTPS support enabled via gRPC's OpenSSL (Gemini + HTTPS)")
   endif()
 endif()
 
@@ -141,6 +153,11 @@ if(YAZE_WITH_GRPC)
     libprotobuf
   )
   
+  # On Windows, force whole-archive linking for protobuf to ensure all symbols are included
+  if(MSVC)
+    target_link_options(yaze_agent PUBLIC /WHOLEARCHIVE:libprotobuf)
+  endif()
+  
   # Note: YAZE_WITH_GRPC is defined globally via add_compile_definitions in root CMakeLists.txt
   # This ensures #ifdef YAZE_WITH_GRPC works in all translation units
   message(STATUS "✓ gRPC GUI automation enabled for yaze_agent")
diff --git a/src/cli/z3ed.cmake b/src/cli/z3ed.cmake
index 44b85eae..5bfffa33 100644
--- a/src/cli/z3ed.cmake
+++ b/src/cli/z3ed.cmake
@@ -40,4 +40,9 @@ endif()
 if(YAZE_WITH_GRPC)
   message(STATUS "Adding gRPC support to z3ed CLI")
   target_link_libraries(z3ed PRIVATE grpc++ grpc++_reflection libprotobuf)
+  
+  # On Windows, force whole-archive linking for protobuf to ensure all symbols are included
+  if(MSVC)
+    target_link_options(z3ed PRIVATE /WHOLEARCHIVE:libprotobuf)
+  endif()
 endif()
\ No newline at end of file