diff --git a/.github/workflows/trybot.yaml b/.github/workflows/trybot.yaml
index a8fe3b5b6..5fab75d43 100644
--- a/.github/workflows/trybot.yaml
+++ b/.github/workflows/trybot.yaml
@@ -234,3 +234,11 @@ jobs:
           ALGOLIA_INDEX_FILE: ../_public/algolia.json
       - name: 'tip.cuelang.org: Apply tip''s patch, checking that it applies cleanly'
         run: _scripts/tipPatchApply.bash
+      - if: github.repository == 'cue-lang/cuelang.org' && (github.ref == 'refs/heads/master' || (github.ref == 'refs/heads/ci/test'))
+        name: 'tip.cuelang.org: Resolve the tip version of cue-lang/cue and configure the site to use it'
+        run: _scripts/tipUseAlternativeCUE.bash
+        env:
+          GOPROXY: direct
+      - 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
diff --git a/_scripts/tipUseAlternativeCUE.bash b/_scripts/tipUseAlternativeCUE.bash
new file mode 100755
index 000000000..2f9167669
--- /dev/null
+++ b/_scripts/tipUseAlternativeCUE.bash
@@ -0,0 +1,44 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+# Usage:
+#     tipUseAlternativeCUE.bash [CUE_COMMIT_REF]
+#
+# tipUseAlternativeCUE resolves the version of CUE available via
+# cuelang.org/go@$CUE_COMMIT_REF and overrides the site configuration so that
+# this version takes the place of all named CUEs (currently only "latest" and
+# "prerelease" are directly overridden, with their versions transitively
+# dictating those used by "tip", "default", and "playground"). CUE_COMMIT_REF
+# defaults to "master", so that invoking the script with no arguments will use
+# the tip of cue-lang/cue.
+
+versionRef=${1:-master}
+
+# cd to the parent directory to that containing the script
+cd "$( cd "$( dirname "${BASH_SOURCE[0]}" )" >/dev/null 2>&1 && pwd )/.."
+
+# Resolve $versionRef to a pseudo-version. Notice this intentionally honours
+# GOPROXY rather that setting a specific value in the script, allowing the
+# setting to be controlled by this script's invocation.
+td=$(mktemp -d)
+trap "rm -rf $td" EXIT
+pushd $td > /dev/null
+go mod init mod.example &> /dev/null
+go get cuelang.org/go@$versionRef &> /dev/null
+version=$(go list -m -f={{.Version}} cuelang.org/go)
+popd > /dev/null
+
+echo "Will use cuelang.org/go@$version"
+
+# Override all versions of CUE referenced by the site to be $version.
+# This might change if any entries are added to the version matrix that
+# deliberately make a previous version of CUE available but, for now, we don't
+# need that - and could easily make it configurable later.
+go run cuelang.org/go/cmd/cue def \
+    -t version="$version" \
+    -p site \
+    --out cue \
+    cue: - <<EOD >tip.cue
+_version: _ @tag(version)
+versions: cue: [string]: v: _version
+EOD
diff --git a/internal/ci/github/trybot.cue b/internal/ci/github/trybot.cue
index bd937c773..a106b54c4 100644
--- a/internal/ci/github/trybot.cue
+++ b/internal/ci/github/trybot.cue
@@ -253,6 +253,24 @@ workflows: trybot: _repo.bashWorkflow & {
 				name: "tip.cuelang.org: Apply tip's patch, checking that it applies cleanly"
 				run:  "_scripts/tipPatchApply.bash"
 			},
+
+			json.#step & {
+				name: "tip.cuelang.org: Resolve the tip version of cue-lang/cue and configure the site to use it"
+				// Only run in the main repo on the default branch or its designated test branch (i.e not CLs)
+				// so that CLs aren't blocked by failures caused by unrelated changes.
+				if: "github.repository == '\(_repo.githubRepositoryPath)' && (github.ref == 'refs/heads/\(_repo.defaultBranch)' || \(_repo.isTestDefaultBranch))"
+				// Force Go to bypass the module proxy, ensuring that the absolute
+				// latest CUE pseudo-version is available to test against.
+				env: GOPROXY: "direct"
+				run: "_scripts/tipUseAlternativeCUE.bash"
+			},
+			json.#step & {
+				name: "tip.cuelang.org: Check if the site builds against the tip of cue-lang/cue"
+				// Only run in the main repo on the default branch or its designated test branch (i.e not CLs)
+				// so that CLs aren't blocked by failures caused by unrelated changes.
+				if:  "github.repository == '\(_repo.githubRepositoryPath)' && (github.ref == 'refs/heads/\(_repo.defaultBranch)' || \(_repo.isTestDefaultBranch))"
+				run: "_scripts/regenPostInfraChange.bash"
+			},
 		]
 	}