diff --git a/Makefile b/Makefile
index f3801e4950c56..e8cdcd3a3a1ba 100644
--- a/Makefile
+++ b/Makefile
@@ -54,6 +54,16 @@ FIND_EXCLUSIONS= \
 	-not \( \( -path '*/.git/*' -o -path './build/*' -o -path './vendor/*' -o -path './.coderv2/*' -o -path '*/node_modules/*' -o -path '*/out/*' -o -path './coderd/apidoc/*' -o -path '*/.next/*' -o -path '*/.terraform/*' \) -prune \)
 # Source files used for make targets, evaluated on use.
 GO_SRC_FILES := $(shell find . $(FIND_EXCLUSIONS) -type f -name '*.go' -not -name '*_test.go')
+# Same as GO_SRC_FILES but excluding certain files that have problematic
+# Makefile dependencies (e.g. pnpm).
+MOST_GO_SRC_FILES := $(shell \
+	find . \
+		$(FIND_EXCLUSIONS) \
+		-type f \
+		-name '*.go' \
+		-not -name '*_test.go' \
+		-not -wholename './agent/agentcontainers/dcspec/dcspec_gen.go' \
+)
 # All the shell files in the repo, excluding ignored files.
 SHELL_SRC_FILES := $(shell find . $(FIND_EXCLUSIONS) -type f -name '*.sh')
 
@@ -243,7 +253,7 @@ $(CODER_ALL_BINARIES): go.mod go.sum \
 	fi
 
 # This task builds Coder Desktop dylibs
-$(CODER_DYLIBS): go.mod go.sum $(GO_SRC_FILES)
+$(CODER_DYLIBS): go.mod go.sum $(MOST_GO_SRC_FILES)
 	@if [ "$(shell uname)" = "Darwin" ]; then
 		$(get-mode-os-arch-ext)
 		./scripts/build_go.sh \
@@ -659,8 +669,12 @@ agent/agentcontainers/acmock/acmock.go: agent/agentcontainers/containers.go
 	go generate ./agent/agentcontainers/acmock/
 	touch "$@"
 
-agent/agentcontainers/dcspec/dcspec_gen.go: agent/agentcontainers/dcspec/devContainer.base.schema.json
-	go generate ./agent/agentcontainers/dcspec/
+agent/agentcontainers/dcspec/dcspec_gen.go: \
+	node_modules/.installed \
+	agent/agentcontainers/dcspec/devContainer.base.schema.json \
+	agent/agentcontainers/dcspec/gen.sh \
+	agent/agentcontainers/dcspec/doc.go
+	DCSPEC_QUIET=true go generate ./agent/agentcontainers/dcspec/
 	touch "$@"
 
 $(TAILNETTEST_MOCKS): tailnet/coordinator.go tailnet/service.go
diff --git a/agent/agentcontainers/dcspec/gen.sh b/agent/agentcontainers/dcspec/gen.sh
index f9d3377d8170c..c74efe2efb0d5 100755
--- a/agent/agentcontainers/dcspec/gen.sh
+++ b/agent/agentcontainers/dcspec/gen.sh
@@ -30,14 +30,36 @@ fi
 
 TMPDIR=$(mktemp -d)
 trap 'rm -rfv "$TMPDIR"' EXIT
-pnpm exec quicktype \
+
+show_stderr=1
+exec 3>&2
+if [[ " $* " == *" --quiet "* ]] || [[ ${DCSPEC_QUIET:-false} == "true" ]]; then
+	# Redirect stderr to log because quicktype can't infer all types and
+	# we don't care right now.
+	show_stderr=0
+	exec 2>"${TMPDIR}/stderr.log"
+fi
+
+if ! pnpm exec quicktype \
 	--src-lang schema \
 	--lang go \
 	--just-types-and-package \
 	--top-level "DevContainer" \
 	--out "${TMPDIR}/${DEST_FILENAME}" \
 	--package "dcspec" \
-	"${SCHEMA_DEST}"
+	"${SCHEMA_DEST}"; then
+	echo "quicktype failed to generate Go code." >&3
+	if [[ "${show_stderr}" -eq 1 ]]; then
+		cat "${TMPDIR}/stderr.log" >&3
+	fi
+	exit 1
+fi
+
+if [[ "${show_stderr}" -eq 0 ]]; then
+	# Restore stderr.
+	exec 2>&3
+fi
+exec 3>&-
 
 # Format the generated code.
 go run mvdan.cc/gofumpt@v0.4.0 -w -l "${TMPDIR}/${DEST_FILENAME}"