diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8baa7ac123..5f60ae70c3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -23,6 +23,7 @@ We use *breaking :warning:* to mark changes that are not backward compatible (re
 ### Fixed
 - [#5281](https://github.com/thanos-io/thanos/pull/5281) Blocks: Use correct separators for filesystem paths and object storage paths respectively.
 - [#5300](https://github.com/thanos-io/thanos/pull/5300) Query: Ignore cache on queries with deduplication off.
+- [#5324](https://github.com/thanos-io/thanos/pull/5324) Reloader: Force trigger reload when config rollbacked
 
 ### Added
 
diff --git a/pkg/reloader/reloader.go b/pkg/reloader/reloader.go
index 6303bba564..4dcf06df74 100644
--- a/pkg/reloader/reloader.go
+++ b/pkg/reloader/reloader.go
@@ -96,6 +96,7 @@ type Reloader struct {
 
 	lastCfgHash         []byte
 	lastWatchedDirsHash []byte
+	forceReload         bool
 
 	reloads                    prometheus.Counter
 	reloadErrors               prometheus.Counter
@@ -352,7 +353,7 @@ func (r *Reloader) apply(ctx context.Context) error {
 		watchedDirsHash = h.Sum(nil)
 	}
 
-	if bytes.Equal(r.lastCfgHash, cfgHash) && bytes.Equal(r.lastWatchedDirsHash, watchedDirsHash) {
+	if !r.forceReload && bytes.Equal(r.lastCfgHash, cfgHash) && bytes.Equal(r.lastWatchedDirsHash, watchedDirsHash) {
 		// Nothing to do.
 		return nil
 	}
@@ -368,6 +369,7 @@ func (r *Reloader) apply(ctx context.Context) error {
 			return errors.Wrap(err, "trigger reload")
 		}
 
+		r.forceReload = false
 		r.lastCfgHash = cfgHash
 		r.lastWatchedDirsHash = watchedDirsHash
 		level.Info(r.logger).Log(
@@ -379,6 +381,7 @@ func (r *Reloader) apply(ctx context.Context) error {
 		r.lastReloadSuccessTimestamp.SetToCurrentTime()
 		return nil
 	}); err != nil {
+		r.forceReload = true
 		level.Error(r.logger).Log("msg", "Failed to trigger reload. Retrying.", "err", err)
 	}
 
diff --git a/pkg/reloader/reloader_test.go b/pkg/reloader/reloader_test.go
index 9367ebfe3b..0b8412273c 100644
--- a/pkg/reloader/reloader_test.go
+++ b/pkg/reloader/reloader_test.go
@@ -167,6 +167,119 @@ config:
 	testutil.Ok(t, os.Unsetenv("TEST_RELOADER_THANOS_ENV2"))
 }
 
+func TestReloader_ConfigRollback(t *testing.T) {
+	ctx, cancel := context.WithTimeout(context.Background(), 3*time.Minute)
+	defer cancel()
+
+	l, err := net.Listen("tcp", "localhost:0")
+	testutil.Ok(t, err)
+
+	correctConfig := []byte(`
+config:
+  a: 1
+`)
+	faultyConfig := []byte(`
+faulty_config:
+  a: 1
+`)
+
+	dir, err := ioutil.TempDir("", "reloader-cfg-test")
+	testutil.Ok(t, err)
+	defer func() { testutil.Ok(t, os.RemoveAll(dir)) }()
+
+	testutil.Ok(t, os.Mkdir(filepath.Join(dir, "in"), os.ModePerm))
+	testutil.Ok(t, os.Mkdir(filepath.Join(dir, "out"), os.ModePerm))
+
+	var (
+		input  = filepath.Join(dir, "in", "cfg.yaml.tmpl")
+		output = filepath.Join(dir, "out", "cfg.yaml")
+	)
+
+	reloads := &atomic.Value{}
+	reloads.Store(0)
+	srv := &http.Server{}
+
+	srv.Handler = http.HandlerFunc(func(resp http.ResponseWriter, r *http.Request) {
+		f, err := ioutil.ReadFile(output)
+		testutil.Ok(t, err)
+
+		if string(f) == string(faultyConfig) {
+			resp.WriteHeader(http.StatusServiceUnavailable)
+			return
+		}
+
+		reloads.Store(reloads.Load().(int) + 1) // The only writer.
+		resp.WriteHeader(http.StatusOK)
+	})
+	go func() { _ = srv.Serve(l) }()
+	defer func() { testutil.Ok(t, srv.Close()) }()
+
+	reloadURL, err := url.Parse(fmt.Sprintf("http://%s", l.Addr().String()))
+	testutil.Ok(t, err)
+
+	reloader := New(nil, nil, &Options{
+		ReloadURL:     reloadURL,
+		CfgFile:       input,
+		CfgOutputFile: output,
+		WatchedDirs:   nil,
+		WatchInterval: 10 * time.Second, // 10 seconds to make the reload of faulty config fail quick
+		RetryInterval: 100 * time.Millisecond,
+		DelayInterval: 1 * time.Millisecond,
+	})
+
+	testutil.Ok(t, ioutil.WriteFile(input, correctConfig, os.ModePerm))
+
+	rctx, cancel2 := context.WithCancel(ctx)
+	g := sync.WaitGroup{}
+	g.Add(1)
+	go func() {
+		defer g.Done()
+		testutil.Ok(t, reloader.Watch(rctx))
+	}()
+
+	reloadsSeen := 0
+	faulty := false
+
+	for {
+		select {
+		case <-ctx.Done():
+			t.Fatalf("Timeout with faulty = %t, reloadsSeen = %d", faulty, reloadsSeen)
+		case <-time.After(300 * time.Millisecond):
+		}
+
+		rel := reloads.Load().(int)
+		reloadsSeen = rel
+
+		if reloadsSeen == 1 && !faulty {
+			// Initial apply seen (without doing anything).
+			f, err := ioutil.ReadFile(output)
+			testutil.Ok(t, err)
+			testutil.Equals(t, string(correctConfig), string(f))
+
+			// Change to a faulty config
+			testutil.Ok(t, ioutil.WriteFile(input, faultyConfig, os.ModePerm))
+			faulty = true
+		} else if reloadsSeen == 1 && faulty {
+			// Faulty config will trigger a reload, but reload failed
+			f, err := ioutil.ReadFile(output)
+			testutil.Ok(t, err)
+			testutil.Equals(t, string(faultyConfig), string(f))
+
+			// Rollback config
+			testutil.Ok(t, ioutil.WriteFile(input, correctConfig, os.ModePerm))
+		} else if reloadsSeen >= 2 {
+			// Rollback to previous config should trigger a reload
+			f, err := ioutil.ReadFile(output)
+			testutil.Ok(t, err)
+			testutil.Equals(t, string(correctConfig), string(f))
+
+			break
+		}
+	}
+	cancel2()
+	g.Wait()
+}
+
 func TestReloader_DirectoriesApply(t *testing.T) {
 	l, err := net.Listen("tcp", "localhost:0")
 	testutil.Ok(t, err)