diff --git a/src/settings/Settings.tsx b/src/settings/Settings.tsx
index f9de96dbf21..351df6d62a7 100644
--- a/src/settings/Settings.tsx
+++ b/src/settings/Settings.tsx
@@ -230,7 +230,7 @@ export const SETTINGS: { [setting: string]: ISetting } = {
         controller: new ServerSupportUnstableFeatureController(
             "feature_exploring_public_spaces",
             defaultWatchManager,
-            ["org.matrix.msc3827.stable"],
+            [["org.matrix.msc3827.stable"]],
             undefined,
             _td("Requires your server to support the stable version of MSC3827"),
         ),
@@ -372,7 +372,7 @@ export const SETTINGS: { [setting: string]: ISetting } = {
         controller: new ServerSupportUnstableFeatureController(
             "feature_jump_to_date",
             defaultWatchManager,
-            ["org.matrix.msc3030"],
+            [["org.matrix.msc3030"], ["org.matrix.msc3030.stable"]],
             "v1.6",
             _td("Requires your server to support MSC3030"),
         ),
@@ -388,7 +388,7 @@ export const SETTINGS: { [setting: string]: ISetting } = {
         controller: new ServerSupportUnstableFeatureController(
             "sendReadReceipts",
             defaultWatchManager,
-            ["org.matrix.msc2285.stable"],
+            [["org.matrix.msc2285.stable"]],
             "v1.4",
             _td("Your server doesn't support disabling sending read receipts."),
             true,
diff --git a/src/settings/controllers/ServerSupportUnstableFeatureController.ts b/src/settings/controllers/ServerSupportUnstableFeatureController.ts
index 7dfe4bb69c4..b6022afbb90 100644
--- a/src/settings/controllers/ServerSupportUnstableFeatureController.ts
+++ b/src/settings/controllers/ServerSupportUnstableFeatureController.ts
@@ -26,12 +26,21 @@ import SettingsStore from "../SettingsStore";
  * When a setting gets disabled or enabled from this controller it notifies the given WatchManager
  */
 export default class ServerSupportUnstableFeatureController extends MatrixClientBackedController {
+    // Starts off as `undefined` so when we first compare the `newDisabledValue`, it sees
+    // it as a change and updates the watchers.
     private enabled: boolean | undefined;
 
+    /**
+     * Construct a new ServerSupportUnstableFeatureController.
+     *
+     * @param unstableFeatureGroups - If any one of the feature groups is satisfied,
+     * then the setting is considered enabled. A feature group is satisfied if all of
+     * the features in the group are supported (all features in a group are required).
+     */
     public constructor(
         private readonly settingName: string,
         private readonly watchers: WatchManager,
-        private readonly unstableFeatures: string[],
+        private readonly unstableFeatureGroups: string[][],
         private readonly stableVersion?: string,
         private readonly disabledMessage?: string,
         private readonly forcedValue: any = false,
@@ -43,9 +52,9 @@ export default class ServerSupportUnstableFeatureController extends MatrixClient
         return !this.enabled;
     }
 
-    public set disabled(v: boolean) {
-        if (!v === this.enabled) return;
-        this.enabled = !v;
+    public set disabled(newDisabledValue: boolean) {
+        if (!newDisabledValue === this.enabled) return;
+        this.enabled = !newDisabledValue;
         const level = SettingsStore.firstSupportedLevel(this.settingName);
         if (!level) return;
         const settingValue = SettingsStore.getValue(this.settingName, null);
@@ -53,19 +62,33 @@ export default class ServerSupportUnstableFeatureController extends MatrixClient
     }
 
     protected async initMatrixClient(oldClient: MatrixClient, newClient: MatrixClient): Promise<void> {
-        this.disabled = true;
-        let supported = true;
-
+        // Check for stable version support first
         if (this.stableVersion && (await this.client.isVersionSupported(this.stableVersion))) {
             this.disabled = false;
             return;
         }
-        for (const feature of this.unstableFeatures) {
-            supported = await this.client.doesServerSupportUnstableFeature(feature);
-            if (!supported) break;
+
+        // Otherwise, only one of the unstable feature groups needs to be satisfied in
+        // order for this setting overall to be enabled
+        let isEnabled = false;
+        for (const featureGroup of this.unstableFeatureGroups) {
+            const featureSupportList = await Promise.all(
+                featureGroup.map(async (feature) => {
+                    const isFeatureSupported = await this.client.doesServerSupportUnstableFeature(feature);
+                    return isFeatureSupported;
+                }),
+            );
+
+            // Every feature in a feature group is required in order
+            // for this setting overall to be enabled.
+            const isFeatureGroupSatisfied = featureSupportList.every((isFeatureSupported) => isFeatureSupported);
+            if (isFeatureGroupSatisfied) {
+                isEnabled = true;
+                break;
+            }
         }
 
-        this.disabled = !supported;
+        this.disabled = !isEnabled;
     }
 
     public getValueOverride(
diff --git a/test/settings/controllers/ServerSupportUnstableFeatureController-test.ts b/test/settings/controllers/ServerSupportUnstableFeatureController-test.ts
index bff87d93b29..8fe676d2b0b 100644
--- a/test/settings/controllers/ServerSupportUnstableFeatureController-test.ts
+++ b/test/settings/controllers/ServerSupportUnstableFeatureController-test.ts
@@ -55,7 +55,7 @@ describe("ServerSupportUnstableFeatureController", () => {
             const controller = new ServerSupportUnstableFeatureController(
                 setting,
                 watchers,
-                ["feature"],
+                [["feature"]],
                 undefined,
                 undefined,
                 "other_value",
@@ -74,7 +74,7 @@ describe("ServerSupportUnstableFeatureController", () => {
             const controller = new ServerSupportUnstableFeatureController(
                 setting,
                 watchers,
-                ["feature"],
+                [["feature"]],
                 "other_value",
             );
             await prepareSetting(cli, controller);
@@ -84,38 +84,65 @@ describe("ServerSupportUnstableFeatureController", () => {
     });
 
     describe("settingDisabled()", () => {
-        it("returns true if there is no matrix client", () => {
-            const controller = new ServerSupportUnstableFeatureController(setting, watchers, ["org.matrix.msc3030"]);
+        it("considered disabled if there is no matrix client", () => {
+            const controller = new ServerSupportUnstableFeatureController(setting, watchers, [["org.matrix.msc3030"]]);
             expect(controller.settingDisabled).toEqual(true);
         });
 
-        it("returns true if not all required features are supported", async () => {
+        it("considered disabled if not all required features in the only feature group are supported", async () => {
             const cli = stubClient();
             cli.doesServerSupportUnstableFeature = jest.fn(async (featureName) => {
                 return featureName === "org.matrix.msc3827.stable";
             });
 
             const controller = new ServerSupportUnstableFeatureController(setting, watchers, [
-                "org.matrix.msc3827.stable",
-                "org.matrix.msc3030",
+                ["org.matrix.msc3827.stable", "org.matrix.msc3030"],
             ]);
             await prepareSetting(cli, controller);
 
             expect(controller.settingDisabled).toEqual(true);
         });
 
-        it("returns false if all required features are supported", async () => {
+        it("considered enabled if all required features in the only feature group are supported", async () => {
             const cli = stubClient();
             cli.doesServerSupportUnstableFeature = jest.fn(async (featureName) => {
                 return featureName === "org.matrix.msc3827.stable" || featureName === "org.matrix.msc3030";
             });
             const controller = new ServerSupportUnstableFeatureController(setting, watchers, [
-                "org.matrix.msc3827.stable",
-                "org.matrix.msc3030",
+                ["org.matrix.msc3827.stable", "org.matrix.msc3030"],
             ]);
             await prepareSetting(cli, controller);
 
             expect(controller.settingDisabled).toEqual(false);
         });
+
+        it("considered enabled if all required features in one of the feature groups are supported", async () => {
+            const cli = stubClient();
+            cli.doesServerSupportUnstableFeature = jest.fn(async (featureName) => {
+                return featureName === "org.matrix.msc3827.stable" || featureName === "org.matrix.msc3030";
+            });
+            const controller = new ServerSupportUnstableFeatureController(setting, watchers, [
+                ["foo-unsupported", "bar-unsupported"],
+                ["org.matrix.msc3827.stable", "org.matrix.msc3030"],
+            ]);
+            await prepareSetting(cli, controller);
+
+            expect(controller.settingDisabled).toEqual(false);
+        });
+
+        it("considered disabled if not all required features in one of the feature groups are supported", async () => {
+            const cli = stubClient();
+            cli.doesServerSupportUnstableFeature = jest.fn(async (featureName) => {
+                return featureName === "org.matrix.msc3827.stable";
+            });
+
+            const controller = new ServerSupportUnstableFeatureController(setting, watchers, [
+                ["foo-unsupported", "bar-unsupported"],
+                ["org.matrix.msc3827.stable", "org.matrix.msc3030"],
+            ]);
+            await prepareSetting(cli, controller);
+
+            expect(controller.settingDisabled).toEqual(true);
+        });
     });
 });