diff --git a/.github/workflows/publish_to_dockerhub.yml b/.github/workflows/publish_to_dockerhub.yml
index 741d9acff3..b1a5812e06 100644
--- a/.github/workflows/publish_to_dockerhub.yml
+++ b/.github/workflows/publish_to_dockerhub.yml
@@ -15,11 +15,11 @@ on:
   workflow_dispatch:
     inputs:
       ref:
-        description: 'Ref to build Docker image [default: latest master; examples: v0.92.0, 0a4ff9d3e4a9ab432fd5812eb18c98e03b5a7432]'
+        description: 'Ref to build Docker images for Ubuntu and Windows Server Core [default: latest master; examples: v0.92.0, 0a4ff9d3e4a9ab432fd5812eb18c98e03b5a7432]'
         required: false
         default: ''
       push_image:
-        description: 'Push image to DockerHub [default: false; examples: true, false]'
+        description: 'Push images to DockerHub [default: false; examples: true, false]'
         required: false
         default: 'false'
 
@@ -29,8 +29,8 @@ env:
 
 # A workflow run.
 jobs:
-  test:
-    name: Run tests before publishing
+  tests_ubuntu:
+    name: Run Ubuntu-based tests before publishing
     runs-on: ubuntu-20.04
 
     steps:
@@ -70,10 +70,10 @@ jobs:
 
       - name: Run tests
         run: make test
-  publish:
+  publish_ubuntu:
     # Ensure test job passes before pushing image.
-    needs: test
-    name: Publish image to DockerHub
+    needs: test_ubuntu
+    name: Publish Ubuntu-based image to DockerHub
     runs-on: ubuntu-20.04
     steps:
       - name: Checkout (manual run)
@@ -91,6 +91,52 @@ jobs:
           # Allows to fetch all history for all branches and tags. Need this for proper versioning.
           fetch-depth: 0
 
+      - name: Build image
+        run: make image
+
+      - name: Build image with 'latest' tag
+        if: ${{ github.event_name == 'release' && github.event.release.target_commitish == 'master' }}
+        run: make image-latest
+
+      - name: Login to DockerHub
+        uses: docker/login-action@v1
+        with:
+          username: ${{ secrets.DOCKERHUB_USERNAME }}
+          password: ${{ secrets.DOCKERHUB_PASSWORD }}
+
+      - name: Push image to registry
+        if: ${{ github.event_name == 'release' || (github.event_name == 'workflow_dispatch' && github.event.inputs.push_image == 'true') }}
+        run: make image-push
+
+      - name: Push image with 'latest' tag to registry
+        if: ${{ github.event_name == 'release' && github.event.release.target_commitish == 'master' }}
+        run: make image-push-latest
+
+  tests_wsc:
+    name: Run WindowsServerCore-based tests before publishing
+    runs-on: windows-2022
+
+    steps:
+      - name: Checkout (manual run)
+        if: ${{ github.event_name == 'workflow_dispatch' }}
+        uses: actions/checkout@v2
+        with:
+          ref: ${{ github.event.inputs.ref }}
+          # Allows to fetch all history for all branches and tags. Need this for proper versioning.
+          fetch-depth: 0
+
+      - name: Checkout (automatical run)
+        if: ${{ github.event_name != 'workflow_dispatch' }}
+        uses: actions/checkout@v2
+        with:
+          # Allows to fetch all history for all branches and tags. Need this for proper versioning.
+          fetch-depth: 0
+
+      - name: Sync VM submodule
+        run: |
+          git submodule sync
+          git submodule update --init
+
       - name: Set up Go
         uses: actions/setup-go@v2
         with:
@@ -105,12 +151,34 @@ jobs:
       - name: Update Go modules
         run: go mod download -json
 
-      - name: Build image
-        run: make image
+      - name: Run tests
+        run: make test
+  publish_wsc:
+    # Ensure test job passes before pushing image.
+    # TODO: currently test_wsc job is failing, so we have `always()` condition.
+    # After #2269 and #2268 this condition should be removed.
+    if: ${{ always() }}
+    needs: test_wsc
+    name: Publish WindowsServerCore-based image to DockerHub
+    runs-on: windows-2022
+    steps:
+      - name: Checkout (manual run)
+        if: ${{ github.event_name == 'workflow_dispatch' }}
+        uses: actions/checkout@v2
+        with:
+          ref: ${{ github.event.inputs.ref }}
+          # Allows to fetch all history for all branches and tags. Need this for proper versioning.
+          fetch-depth: 0
 
-      - name: Build image with 'latest' tag
-        if: ${{ github.event_name == 'release' && github.event.release.target_commitish == 'master' }}
-        run: make image-latest
+      - name: Checkout (automatical run)
+        if: ${{ github.event_name != 'workflow_dispatch' }}
+        uses: actions/checkout@v2
+        with:
+          # Allows to fetch all history for all branches and tags. Need this for proper versioning.
+          fetch-depth: 0
+
+      - name: Build image
+        run: make image-wsc
 
       - name: Login to DockerHub
         uses: docker/login-action@v1
@@ -120,8 +188,4 @@ jobs:
 
       - name: Push image to registry
         if: ${{ github.event_name == 'release' || (github.event_name == 'workflow_dispatch' && github.event.inputs.push_image == 'true') }}
-        run: make image-push
-
-      - name: Push image with 'latest' tag to registry
-        if: ${{ github.event_name == 'release' && github.event.release.target_commitish == 'master' }}
-        run: make image-push-latest
+        run: make image-wsc-push
diff --git a/Makefile b/Makefile
index 0ca1116a74..2099b5248b 100644
--- a/Makefile
+++ b/Makefile
@@ -18,7 +18,7 @@ IMAGE_REPO=nspccdev/neo-go
 
 # All of the targets are phony here because we don't really use make dependency
 # tracking for files
-.PHONY: build deps image image-wsc image-latest image-push image-push-latest check-version clean-cluster push-tag \
+.PHONY: build deps image image-wsc image-latest image-push image-wsc-push image-push-latest check-version clean-cluster push-tag \
 	test vet lint fmt cover
 
 build: deps
@@ -61,11 +61,15 @@ image-latest: deps
 	@docker build -t $(IMAGE_REPO):latest --build-arg REPO=$(REPO) --build-arg VERSION=$(VERSION) .
 
 image-push:
-	@echo "=> Publish image"
+	@echo "=> Publish image for Ubuntu"
 	@docker push $(IMAGE_REPO):$(VERSION)
 
+image-wsc-push:
+	@echo "=> Publish image for Windows Server Core"
+	@docker push $(IMAGE_REPO):$(VERSION)_WindowsServerCore
+
 image-push-latest:
-	@echo "=> Publish image with 'latest' tag"
+	@echo "=> Publish image for Ubuntu with 'latest' tag"
 	@docker push $(IMAGE_REPO):latest
 
 check-version: