diff --git a/cmd/dry_run_contract_test.go b/cmd/dry_run_contract_test.go
new file mode 100644
index 0000000..6b56190
--- /dev/null
+++ b/cmd/dry_run_contract_test.go
@@ -0,0 +1,173 @@
+// Copyright © 2026 Dropbox, Inc.
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+//     http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+
+package cmd
+
+import (
+	"slices"
+	"sort"
+	"strings"
+	"testing"
+
+	"github.com/spf13/cobra"
+)
+
+// dryRunCommands is the expected set of structured-output commands that expose
+// a --dry-run flag. It anchors the cross-command dry-run contract: adding
+// --dry-run to one of those commands means adding it here, which forces the
+// coupled edits (flag registration, input schema, planned status) to be
+// verified together instead of drifting apart.
+//
+// Per-command tests already cover the runtime behavior (planned JSON/text
+// output, and that no write API is called). This registry guards the
+// invariants that span all of them at once, so a new dry-run command cannot
+// silently skip one of the conventions.
+var dryRunCommands = []string{
+	"cp",
+	"mkdir",
+	"mv",
+	"put",
+	"restore",
+	"rm",
+	"share-link create",
+	"share-link revoke",
+	"share-link update",
+}
+
+// TestDryRunRegistryMatchesRegisteredFlags asserts the registry and the set of
+// structured-output commands that actually register --dry-run are exactly
+// equal. This catches both directions of drift for dry-run commands that are
+// expected to publish the JSON contract checked below.
+func TestDryRunRegistryMatchesRegisteredFlags(t *testing.T) {
+	registered := commandsWithDryRunFlag(t)
+
+	want := append([]string{}, dryRunCommands...)
+	sort.Strings(want)
+	got := append([]string{}, registered...)
+	sort.Strings(got)
+
+	if !slices.Equal(got, want) {
+		t.Fatalf("commands with --dry-run = %v, want registry %v", got, want)
+	}
+}
+
+// TestDryRunCommandsDeclarePlannedStatus asserts every dry-run command allows
+// the "planned" result status in both its manifest contract metadata and its
+// code-derived JSON schema. Without this a dry-run branch could emit a
+// "planned" result that fails schema validation for consumers.
+func TestDryRunCommandsDeclarePlannedStatus(t *testing.T) {
+	schemas := jsonCommandSchemas()
+
+	for _, command := range dryRunCommands {
+		contract, ok := commandContractRegistry[command]
+		if !ok {
+			t.Errorf("dry-run command %q has no contract registry entry", command)
+		} else if !slices.Contains(contract.Statuses, jsonStatusPlanned) {
+			t.Errorf("dry-run command %q contract statuses = %v, want to include %q", command, contract.Statuses, jsonStatusPlanned)
+		}
+
+		schema, ok := schemas[command]
+		if !ok {
+			t.Errorf("dry-run command %q has no code-derived schema", command)
+			continue
+		}
+		if !slices.Contains(schema.Statuses, jsonStatusPlanned) {
+			t.Errorf("dry-run command %q schema statuses = %v, want to include %q", command, schema.Statuses, jsonStatusPlanned)
+		}
+	}
+}
+
+// TestDryRunCommandsExposeDryRunInInputSchema asserts every dry-run command
+// advertises a dry_run property in its published input schema, so machine
+// consumers can discover the flag.
+func TestDryRunCommandsExposeDryRunInInputSchema(t *testing.T) {
+	for _, command := range dryRunCommands {
+		cmd := findCommandByPath(t, command)
+		meta := commandManifestMetadataFor(command)
+		flags := jsonCommandFlags(cmd, meta.Flags)
+		schema := commandInputSchemaFor(meta.Args, commandInputSchemaFlags(cmd, flags))
+		if _, ok := schema.Properties["dry_run"]; !ok {
+			t.Errorf("dry-run command %q input schema properties = %v, want to include dry_run", command, inputSchemaPropertyNames(schema))
+		}
+	}
+}
+
+// TestDryRunCommandsExposeDryRunInResultInputSchema asserts every dry-run
+// command uses a result input schema that carries dry_run too. This keeps the
+// runtime JSON convention machine-checkable: dry-run is visible both at the
+// command input level and on each planned operation result.
+func TestDryRunCommandsExposeDryRunInResultInputSchema(t *testing.T) {
+	schemas := jsonCommandSchemas()
+	definitions := jsonContractDefinitions()
+
+	for _, command := range dryRunCommands {
+		schema, ok := schemas[command]
+		if !ok {
+			t.Errorf("dry-run command %q has no code-derived schema", command)
+			continue
+		}
+		if schema.ResultInput == nil {
+			t.Errorf("dry-run command %q result input schema = nil, want schema with dry_run", command)
+			continue
+		}
+
+		resultInput := *schema.ResultInput
+		fields, ok := definitions[resultInput]
+		if !ok {
+			t.Errorf("dry-run command %q result input schema %q has no definition", command, resultInput)
+			continue
+		}
+		if !slices.Contains(fields, "dry_run") {
+			t.Errorf("dry-run command %q result input schema %q fields = %v, want to include dry_run", command, resultInput, fields)
+		}
+	}
+}
+
+func commandsWithDryRunFlag(t *testing.T) []string {
+	t.Helper()
+
+	var commands []string
+	// Dry-run currently belongs to structured-output mutation commands. If a
+	// non-structured command grows --dry-run, that command should first define a
+	// JSON contract so the dry-run schema invariants below can cover it.
+	for _, path := range structuredOutputCommandPaths(RootCmd) {
+		cmd := findCommandByPath(t, path)
+		if cmd.Flags().Lookup(dryRunFlagName) != nil {
+			commands = append(commands, path)
+		}
+	}
+	return commands
+}
+
+func findCommandByPath(t *testing.T, path string) *cobra.Command {
+	t.Helper()
+
+	cmd, _, err := RootCmd.Find(strings.Split(path, " "))
+	if err != nil {
+		t.Fatalf("find command %q: %v", path, err)
+	}
+	if cmd == RootCmd {
+		t.Fatalf("command %q resolved to root", path)
+	}
+	return cmd
+}
+
+func inputSchemaPropertyNames(schema jsonCommandInputSchema) []string {
+	names := make([]string, 0, len(schema.Properties))
+	for name := range schema.Properties {
+		names = append(names, name)
+	}
+	sort.Strings(names)
+	return names
+}