diff --git a/.github/workflows/trybot.yaml b/.github/workflows/trybot.yaml
index ae4241482..266723277 100644
--- a/.github/workflows/trybot.yaml
+++ b/.github/workflows/trybot.yaml
@@ -241,3 +241,6 @@ jobs:
       - if: github.repository == 'cue-lang/cuelang.org' && (github.ref == 'refs/heads/master' || (github.ref == 'refs/heads/ci/test'))
         name: 'tip.cuelang.org: Check if the site builds against the tip of cue-lang/cue'
         run: _scripts/regenPostInfraChange.bash
+      - if: github.repository == 'cue-lang/cuelang.org' && (github.ref == 'refs/heads/master' || (github.ref == 'refs/heads/ci/test'))
+        name: 'tip.cuelang.org: Deploy the site'
+        run: _scripts/tipDeploy.bash
diff --git a/_scripts/tipDeploy.bash b/_scripts/tipDeploy.bash
new file mode 100755
index 000000000..cc1173266
--- /dev/null
+++ b/_scripts/tipDeploy.bash
@@ -0,0 +1,27 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+# Usage:
+#     tipDeploy.bash
+#
+# tipDeploy commits the current state of the working tree and force-pushes it
+# to the "tip" branch, which triggers a build-and-deploy of tip.cuelang.org
+# inside Netlify.
+
+# cd to the parent directory to that containing the script
+cd "$( dirname "${BASH_SOURCE[0]}" )"
+cd ..
+
+headShortRef=$(git rev-parse --short HEAD)
+
+git add content/**/gen_cache.cue
+git commit --allow-empty --message "tip.cuelang.org: $headShortRef: cache files"
+git add .
+git commit --allow-empty --message "tip.cuelang.org: $headShortRef: source changes"
+
+# A --force push is required because there's no automated *and meaningful* path
+# between the current state of the tip branch and the state we wish to push.
+# We don't lose any information by force pushing to this branch, whose only
+# purpose is to communicate the state that needs to be deployed and to act as a
+# trigger for the build inside Netlify.
+git push --force origin HEAD:tip
diff --git a/internal/ci/github/trybot.cue b/internal/ci/github/trybot.cue
index 7397b5d8a..e62296427 100644
--- a/internal/ci/github/trybot.cue
+++ b/internal/ci/github/trybot.cue
@@ -271,6 +271,12 @@ workflows: trybot: _repo.bashWorkflow & {
 				if:  "github.repository == '\(_repo.githubRepositoryPath)' && (github.ref == 'refs/heads/\(_repo.defaultBranch)' || \(_repo.isTestDefaultBranch))"
 				run: "_scripts/regenPostInfraChange.bash"
 			},
+			json.#step & {
+				name: "tip.cuelang.org: Deploy the site"
+				// Only run in the main repo on the default branch or its designated test branch.
+				if:  "github.repository == '\(_repo.githubRepositoryPath)' && (github.ref == 'refs/heads/\(_repo.defaultBranch)' || \(_repo.isTestDefaultBranch))"
+				run: "_scripts/tipDeploy.bash"
+			},
 		]
 	}