diff --git a/docs/design_docs/tweak_compatibility.md b/docs/design_docs/tweak_compatibility.md
index 1e9c931b..965e5f3b 100644
--- a/docs/design_docs/tweak_compatibility.md
+++ b/docs/design_docs/tweak_compatibility.md
@@ -69,8 +69,10 @@ Central replication can assess an effective value which differs from a saved
 preference, such as internal Metadata encryption whose prerequisites are inactive.
 Recovery accepts the current saved or effective snapshot without treating that
 representation difference as a settings change. Applying assessed changes retains
-saved preferences for settings whose effective values already agree. The full
-settings signature still detects a preference changed while awaiting a decision.
+saved preferences only when they leave the adopted effective values unchanged.
+If adoption activates encryption prerequisites, the adopted encryption value
+takes precedence. The full settings signature still detects a preference changed
+while awaiting a decision.
 
 The active publication reservation is not held while waiting for the dialogue.
 Remote writes use the failed attempt's publication guard. Fetch and Rebuild use
diff --git a/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.ts b/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.ts
index 0294b7d1..4053b6c9 100644
--- a/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.ts
+++ b/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.ts
@@ -215,8 +215,17 @@ export class ModuleResolvingMismatchedTweaks extends AbstractModule {
     ): Promise<[TweakValues | boolean, boolean]> {
         if (assessment.alignment === "matched") return [false, false];
         if (this.requiresIdConfigurationReview(assessment)) return [false, false];
-        // Retain saved preferences when only their effective representation differs from the assessment.
+        // Retain saved preferences only when they leave the adopted effective values unchanged.
+        const assessedSettings = settingsAfterAdoption(assessment, "adoptPreferred");
         const acceptedSettings = settingsAfterAdoption(assessment, "adoptPreferred", this.settings);
+        if (
+            this.settings.remoteType === REMOTE_COUCHDB &&
+            usesEncryptedInternalMetadata({ ...this.settings, ...acceptedSettings }) !==
+                usesEncryptedInternalMetadata({ ...this.settings, ...assessedSettings })
+        ) {
+            // Adopting encryption prerequisites can activate a previously inactive preference.
+            acceptedSettings.encryptInternalMetadata = assessedSettings.encryptInternalMetadata;
+        }
         const autoAcceptSide = await this._shouldAutoAcceptCompatibleLossy(assessment);
         if (autoAcceptSide === "REMOTE") return [acceptedSettings, false];
         if (autoAcceptSide === "CURRENT") return [true, false];
diff --git a/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.unit.spec.ts b/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.unit.spec.ts
index b8fb8623..f52f5c85 100644
--- a/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.unit.spec.ts
+++ b/src/modules/coreFeatures/ModuleResolveMismatchedTweaks.unit.spec.ts
@@ -14,6 +14,7 @@ import {
     CENTRAL_COMPATIBILITY_REJECTION_REASONS,
     REMOTE_RESOURCE_KINDS,
     USER_INITIATED_REPLICATION_AUTHORITY,
+    usesEncryptedInternalMetadata,
     type ReplicationAttemptFailure,
 } from "@vrtmrz/livesync-commonlib/replication";
 
@@ -74,6 +75,46 @@ function createModule(settingsOverride: Partial<typeof DEFAULT_SETTINGS> = {}) {
 }
 
 describe("ModuleResolvingMismatchedTweaks", () => {
+    it.each([
+        { label: "E2EE", encrypt: false, usePathObfuscation: true },
+        { label: "Property Encryption", encrypt: true, usePathObfuscation: false },
+    ])(
+        "uses the remote Metadata encryption preference when adoption enables $label",
+        async ({ encrypt, usePathObfuscation }) => {
+            const { module, core, askSelectStringDialogue } = createModule({
+                autoAcceptCompatibleTweak: false,
+                encrypt,
+                usePathObfuscation,
+                E2EEAlgorithm: "v2",
+                encryptInternalMetadata: true,
+                idDerivationVersion: 0,
+            });
+            const current = {
+                ...extractObject(TweakValuesTemplate, core.settings),
+                encryptInternalMetadata: usesEncryptedInternalMetadata(core.settings),
+            };
+            const preferred = { ...current, encrypt: true, usePathObfuscation: true, encryptInternalMetadata: false };
+            const assessment = assessTweakCompatibility(current, preferred);
+            core._services.tweakValue = {
+                checkAndAskResolvingMismatched: module._checkAndAskResolvingMismatchedTweaks.bind(module),
+            };
+            core.rebuilder = { $fetchLocal: vi.fn(async () => undefined) };
+            askSelectStringDialogue.mockResolvedValueOnce("Apply settings to this device, and fetch again");
+            const updateRemote = vi.fn(async () => true);
+
+            await expect(module._askResolvingMismatchedTweaks(preferred, updateRemote, assessment)).resolves.toBe(
+                "CHECKAGAIN"
+            );
+
+            expect(core.rebuilder.$fetchLocal).toHaveBeenCalledOnce();
+            expect(core.settings).toMatchObject({ encrypt: true, usePathObfuscation: true });
+            expect(usesEncryptedInternalMetadata(core.settings)).toBe(false);
+            expect(updateRemote).toHaveBeenCalledWith(
+                expect.objectContaining({ encrypt: true, usePathObfuscation: true, encryptInternalMetadata: false })
+            );
+        }
+    );
+
     it.each([
         { label: "automatic alignment with E2EE disabled", autoAcceptCompatibleTweak: true, encrypt: false },
         { label: "manual review with E2EE disabled", autoAcceptCompatibleTweak: false, encrypt: false },