diff --git a/.github/workflows/pr-playground.yml b/.github/workflows/pr-playground.yml
new file mode 100644
index 0000000000..28ea7f55ad
--- /dev/null
+++ b/.github/workflows/pr-playground.yml
@@ -0,0 +1,125 @@
+name: Post Playground link to PR
+on:
+  pull_request_target:
+    types: [labeled]
+  workflow_run:
+    workflows: ["WebAssembly"]
+    types: [completed]
+
+jobs:
+  post-summary:
+    name: Post Playground link
+    runs-on: ubuntu-latest
+    permissions:
+      pull-requests: write
+    # Post a comment only if the PR status check is passed and the PR is labeled with `Playground`.
+    # Triggered twice: when the PR is labeled and when PR build is passed.
+    if: >-
+      ${{ false
+      || (true
+        && github.event_name == 'pull_request_target'
+        && contains(github.event.pull_request.labels.*.name, 'Playground'))
+      || (true
+        && github.event_name == 'workflow_run'
+        && github.event.workflow_run.conclusion == 'success'
+        && github.event.workflow_run.event == 'pull_request'
+      )
+      }}
+    steps:
+      - uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea # v7.0.1
+        with:
+          github-token: ${{ secrets.GITHUB_TOKEN }}
+          script: |
+            const fs = require('fs/promises');
+
+            const buildWorkflowPath = '.github/workflows/wasm.yml';
+            const findSuccessfuBuildRun = async (pr) => {
+              const opts = github.rest.actions.listWorkflowRunsForRepo.endpoint.merge({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                status: 'success',
+                branch: pr.head.ref,
+              });
+              const runs = await github.paginate(opts);
+              const buildRun = runs.find(run => run.path == buildWorkflowPath);
+              return buildRun;
+            }
+
+            const postComment = async (body, pr) => {
+              const { data: comments } = await github.rest.issues.listComments({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: pr.number,
+              });
+
+              const commentOpts = { owner: context.repo.owner, repo: context.repo.repo, body: comment };
+
+              const existingComment = comments.find(comment => comment.body.startsWith(magicComment));
+              if (existingComment) {
+                core.info(`Updating existing comment: ${existingComment.html_url}`);
+                await github.rest.issues.updateComment({
+                  ...commentOpts, comment_id: existingComment.id
+                });
+              } else {
+                await github.rest.issues.createComment({
+                  ...commentOpts, issue_number: pr.number
+                });
+              }
+            }
+
+            const derivePRNumber = async () => {
+              if (context.payload.pull_request) {
+                return context.payload.pull_request.number;
+              }
+              // Workaround for https://github.com/orgs/community/discussions/25220
+
+              console.log(JSON.stringify(context.payload, null, 2));
+              const { data: { artifacts } } = await github.rest.actions.listWorkflowRunArtifacts({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                run_id: context.payload.workflow_run.id,
+              });
+              console.log(JSON.stringify(artifacts, null, 2));
+              const artifact = artifacts.find(artifact => artifact.name == 'github-pr-info');
+              if (!artifact) {
+                throw new Error('Cannot find github-pr-info.txt artifact');
+              }
+
+              const { data } = await github.rest.actions.downloadArtifact({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                artifact_id: artifact.id,
+                archive_format: 'zip',
+              });
+
+              await fs.writeFile('pr-info.zip', Buffer.from(data));
+              await exec.exec('unzip', ['pr-info.zip']);
+              return await fs.readFile('github-pr-info.txt', 'utf8');
+            }
+
+            const prNumber = await derivePRNumber();
+
+            console.log(`PR number: ${prNumber}`);
+            const { data: pr } = await github.rest.pulls.get({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              pull_number: prNumber,
+            });
+
+            core.info(`Checking if the build is successful for ${pr.head.ref} in ${pr.head.repo.owner.login}/${pr.head.repo.name}...`);
+            const buildRun = await findSuccessfuBuildRun(pr);
+            if (!buildRun) {
+              core.info(`No successful build run found for ${buildWorkflowPath} on ${pr.head.ref} yet.`);
+              return;
+            }
+            core.info(`Found a successful build run: ${buildRun.html_url}`);
+
+            const runLink = `${process.env.GITHUB_SERVER_URL}/${process.env.GITHUB_REPOSITORY}/actions/runs/${process.env.GITHUB_RUN_ID}`;
+            const magicComment = `<!-- AUTO-GENERATED-COMMENT-PR-PLAYGROUND -->`;
+            const comment = `${magicComment}
+            **Try on Playground**: https://ruby.github.io/play-ruby?run=${buildRun.id}
+            This is an automated comment by [\`pr-playground.yml\`](${runLink}) workflow.
+            `;
+            core.info(`Comment: ${comment}`);
+            await postComment(comment, pr);
+
diff --git a/.github/workflows/wasm.yml b/.github/workflows/wasm.yml
index f69df0f58d..8c946eb0cb 100644
--- a/.github/workflows/wasm.yml
+++ b/.github/workflows/wasm.yml
@@ -140,6 +140,9 @@ jobs:
         with:
           name: ruby-wasm-install
           path: ${{ github.workspace }}/install.tar.gz
+      - name: Show Playground URL to try the build
+        run: |
+          echo "Try on Playground: https://ruby.github.io/play-ruby?run=$GITHUB_RUN_ID" >> $GITHUB_STEP_SUMMARY
 
       - name: Run basictest
         run: wasmtime run ./../build/miniruby --mapdir /::./ -- basictest/test.rb
@@ -157,6 +160,16 @@ jobs:
           SLACK_WEBHOOK_URL: ${{ secrets.SIMPLER_ALERTS_URL }} # ruby-lang slack: ruby/simpler-alerts-bot
         if: ${{ failure() }}
 
+      # Workaround for https://github.com/orgs/community/discussions/25220
+      - name: Save Pull Request number
+        if: ${{ github.event_name == 'pull_request' }}
+        run: echo "${{ github.event.pull_request.number }}" >> ./github-pr-info.txt
+      - uses: actions/upload-artifact@a8a3f3ad30e3422c9c7b888a15615d19a852ae32 # v3.1.3
+        if: ${{ github.event_name == 'pull_request' }}
+        with:
+          name: github-pr-info
+          path: github-pr-info.txt
+
 defaults:
   run:
     working-directory: build