diff --git a/proto/proto-backplane-grpc/Dockerfile b/proto/proto-backplane-grpc/Dockerfile
index a3645206ea6..6127483c68d 100644
--- a/proto/proto-backplane-grpc/Dockerfile
+++ b/proto/proto-backplane-grpc/Dockerfile
@@ -11,7 +11,10 @@ RUN set -eux; \
   mkdir -p /generated/go; \
   mkdir -p /generated/python; \
   mkdir -p /generated/cpp; \
-  mkdir -p /generated/proto-doc; \
+  mkdir -p /generated/proto-doc/single-html; \
+  mkdir -p /generated/proto-doc/single-md; \
+  mkdir -p /generated/proto-doc/multi-html; \
+  mkdir -p /generated/proto-doc/multi-md; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-grpc=/opt/java/bin/protoc-gen-grpc-java \
     --java_out=/generated/java \
@@ -86,70 +89,153 @@ RUN set -eux; \
     /includes/deephaven/proto/config.proto \
     /includes/deephaven/proto/hierarchicaltable.proto \
     /includes/deephaven/proto/storage.proto; \
-  # proto-doc-gen does not support writing multiple proto files to multiple docs, must break up command
+  # proto-doc-gen does not support writing multiple proto files to multiple docs, must break up command \
+  # we are going to generate 4 sets of docs - single html, multi html, single markdown, multi markdown \
+  # first, single html \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/single-html \
+    --doc_opt=html,index.html \
+    -I/includes \
+    /includes/deephaven/proto/*.proto; \
+  # next, single markdown \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/single-md \
+    --doc_opt=markdown,index.md \
+    -I/includes \
+    /includes/deephaven/proto/*.proto; \
+  # then, multi html \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,ticket.html \
+    -I/includes \
+    /includes/deephaven/proto/ticket.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,console.html \
+    -I/includes \
+    /includes/deephaven/proto/console.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,object.html \
+    -I/includes \
+    /includes/deephaven/proto/object.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,session.html \
+    -I/includes \
+    /includes/deephaven/proto/session.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,table.html \
+    -I/includes \
+    /includes/deephaven/proto/table.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,application.html \
+    -I/includes \
+    /includes/deephaven/proto/application.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,inputtable.html \
+    -I/includes \
+    /includes/deephaven/proto/inputtable.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,partitionedtable.html \
+    -I/includes \
+    /includes/deephaven/proto/partitionedtable.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,config.html \
+    -I/includes \
+    /includes/deephaven/proto/config.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,hierarchicaltable.html \
+    -I/includes \
+    /includes/deephaven/proto/hierarchicaltable.proto; \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-html \
+    --doc_opt=html,storage.html \
+    -I/includes \
+    /includes/deephaven/proto/storage.proto; \
+  # finally, multi md \
+  /opt/protoc/bin/protoc \
+    --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,ticket.md \
     -I/includes \
     /includes/deephaven/proto/ticket.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,console.md \
     -I/includes \
     /includes/deephaven/proto/console.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,object.md \
     -I/includes \
     /includes/deephaven/proto/object.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,session.md \
     -I/includes \
     /includes/deephaven/proto/session.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,table.md \
     -I/includes \
     /includes/deephaven/proto/table.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,application.md \
     -I/includes \
     /includes/deephaven/proto/application.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,inputtable.md \
     -I/includes \
     /includes/deephaven/proto/inputtable.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,partitionedtable.md \
     -I/includes \
     /includes/deephaven/proto/partitionedtable.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,config.md \
     -I/includes \
     /includes/deephaven/proto/config.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,hierarchicaltable.md \
     -I/includes \
     /includes/deephaven/proto/hierarchicaltable.proto; \
   /opt/protoc/bin/protoc \
     --plugin=protoc-gen-doc=/usr/local/bin/protoc-gen-doc \
-    --doc_out=generated/proto-doc \
+    --doc_out=generated/proto-doc/multi-md \
     --doc_opt=markdown,storage.md \
     -I/includes \
     /includes/deephaven/proto/storage.proto; \
diff --git a/proto/proto-backplane-grpc/build.gradle b/proto/proto-backplane-grpc/build.gradle
index fec09f0fa68..17298a0f6cc 100644
--- a/proto/proto-backplane-grpc/build.gradle
+++ b/proto/proto-backplane-grpc/build.gradle
@@ -18,6 +18,7 @@ configurations {
   python {}
   go {}
   cpp {}
+  html {}
   markdown {}
 }
 
@@ -89,7 +90,16 @@ artifacts {
   cpp(layout.buildDirectory.dir('generated/source/proto/main/cpp')) {
     builtBy generateProtobuf
   }
-  markdown(layout.buildDirectory.dir('generated/source/proto/main/proto-doc')) {
+  html(layout.buildDirectory.dir('generated/source/proto/main/proto-doc/single-html')) {
+    builtBy generateProtobuf
+  }
+  html(layout.buildDirectory.dir('generated/source/proto/main/proto-doc/multi-html')) {
+    builtBy generateProtobuf
+  }
+  markdown(layout.buildDirectory.dir('generated/source/proto/main/proto-doc/single-md')) {
+    builtBy generateProtobuf
+  }
+  markdown(layout.buildDirectory.dir('generated/source/proto/main/proto-doc/multi-md')) {
     builtBy generateProtobuf
   }
 }