diff --git a/docs/_may_milestone_.md b/docs/_may_milestone_.md
new file mode 100644
index 000000000000..24c886d4c016
--- /dev/null
+++ b/docs/_may_milestone_.md
@@ -0,0 +1,74 @@
+## Monthly Milestone - May 2020
+
+### Overview
+
+### Goals
+
+- [ ] Migration Guide
+
+  - [ ] Spike: How to migrate LB3 components #4099
+  - [ ] Spike: How to run LB3 app tests when the app is mounted in a LB4 project
+        #5004
+    - [ ] Follow up stories from #5004 if it's done in April.
+
+- [ ] Feature Parity
+
+  - [ ] Model.toObject() should preserve prototypes (e.g. Date and ObjectID
+        values) #3607
+  - [ ] 🏃Custom visual style of REST API Explorer #2023
+
+- [ ] Bugs
+
+  - [ ] defining a nested array model property using @property.array decorator
+        crashes the app #4754
+
+- [ ] Docs / Blogs
+
+  - [ ] :running: Blog on what LB can offer on top of Express #4852
+  - [ ] [Docs] Add debug string information #4845
+  - [ ] [Docs] Add "error handling" page #4846
+  - [ ] [Blog] Managing your APIs: From LoopBack to IBM API Connect #4901
+
+- [ ] Miscellaneous
+
+  - [ ] How to build models, repositories and controllers dynamically at runtime
+        #4296
+  - [ ] Spike: robust handling of ObjectID type for MongoDB #3456
+  - [ ] Integration with TypeORM #4853
+
+- [ ] PRs to review
+  - [ ] feat(repository): hasManyThrough #4438
+  - [ ] [RFC] Enable parallel mocha testing #5011
+  - [ ] feat(http-server): adds http/2 support #4989
+
+### Stretch Goals
+
+- [ ] Docs / Blogs
+
+  - [ ] [Docs] Add "project layout reference" page #4847
+  - [ ] [Docs] Postgresql connector docs should cover LB4 content #4877
+  - [ ] [Docs] MongoDB connector docs should cover LB4 content #4879
+
+- [ ] Bugs
+
+  - [ ] Failed to exclude properties by setting false in `fields` filter via url
+        #4992
+
+- [ ] From relation definition to REST API #2483
+
+  - [ ] [SPIKE] HasMany relation definition to REST API with auto-generated
+        repository/controller classes #3896
+
+- [ ] 🏃Enable TypeScript Project References #2609
+
+### Community Contribution
+
+- [ ] :running: [Spike] How to migrate Angular 1.x and 2+ LB3 client #4610
+- [ ] :running: Document how to send emails in LB4 #1979
+- [ ] :running: Polymorphic relation type #2487
+- [ ] Model.toObject() should preserve prototypes (e.g. Date and ObjectID
+      values) #3607
+- [ ] 🏃 Add bearer auth scheme as the default security scheme #4386
+- [ ] OpenAPI schema generation and model inheritance #3293
+- [ ] default values added for new required columns when running autoupdate()
+      strongloop/loopback-connector-postgresql#418