diff --git a/server/api/bot.go b/server/api/bot.go
index f65891b8a6..22179bf2aa 100644
--- a/server/api/bot.go
+++ b/server/api/bot.go
@@ -199,8 +199,6 @@ func (h *BotHandler) connect(c *Context, w http.ResponseWriter, r *http.Request)
 	} else if app.ShouldSendDailyDigestMessage(info, timezone, currentTime) {
 		sendRegularDigest(DigestSenderParams{isWeekly: false})
 	}
-
-	w.WriteHeader(http.StatusOK)
 }
 
 func (h *BotHandler) createDigestSender(c *Context, w http.ResponseWriter, userID string, userInfo *app.UserInfo) func(DigestSenderParams) {
diff --git a/server/api_bot_test.go b/server/api_bot_test.go
index fe7afd26af..8b0f4c2c48 100644
--- a/server/api_bot_test.go
+++ b/server/api_bot_test.go
@@ -10,6 +10,7 @@ import (
 	"testing"
 
 	"github.com/stretchr/testify/assert"
+	"github.com/stretchr/testify/require"
 
 	"github.com/mattermost/mattermost/server/public/model"
 )
@@ -53,3 +54,54 @@ func TestTrialLicences(t *testing.T) {
 		assert.Equal(t, http.StatusOK, resp.StatusCode)
 	})
 }
+
+// TestBotConnect exercises the real GET /bot/connect endpoint end-to-end (real server, real
+// UserInfoStore and PlaybookRunService — no mocks), confirming it returns 200 in the conditions
+// it handles. The weekly/daily digest-timing decision itself is unit-tested in
+// app/regular_digest_service_test.go; this only confirms the handler reaches a 200 either way.
+func TestBotConnect(t *testing.T) {
+	e := Setup(t)
+	e.CreateBasic()
+
+	// e.RegularUser already owns BasicRun from e.CreateBasic() (via CreateBasicRun()), so
+	// there's something to digest here without any extra setup.
+	botUser, _, err := e.ServerAdminClient.GetUserByUsername(context.Background(), "playbooks", "")
+	require.NoError(t, err)
+
+	dmChannel, _, err := e.ServerClient.CreateDirectChannel(context.Background(), botUser.Id, e.RegularUser.Id)
+	require.NoError(t, err)
+
+	var digestPost *model.Post
+
+	t.Run("digest due for a user connecting for the first time", func(t *testing.T) {
+		resp, err := e.DoPluginAPIRequestWithHeaders(context.Background(), e.ServerClient, http.MethodGet, "/api/v0/bot/connect", "", nil)
+		require.NoError(t, err)
+		assert.Equal(t, http.StatusOK, resp.StatusCode)
+
+		// The bot posts the digest DM synchronously within connect() (Bot.DM ->
+		// pluginAPI.Post.CreatePost, no goroutine/queue), so it's already there by the
+		// time the HTTP response comes back — no need to poll or wait for it.
+		posts, _, err := e.ServerClient.GetPostsForChannel(context.Background(), dmChannel.Id, 0, 10, "", false, false)
+		require.NoError(t, err)
+		require.NotEmpty(t, posts.Order, "expected the bot to have DMed a digest")
+		digestPost = posts.Posts[posts.Order[0]]
+		assert.Equal(t, botUser.Id, digestPost.UserId)
+		assert.NotEmpty(t, digestPost.Message)
+	})
+
+	t.Run("no digest due immediately after the first connect", func(t *testing.T) {
+		// The first subtest's connect() call already persisted LastDailyTodoDMAt = now,
+		// so calling connect() again moments later deterministically finds both
+		// ShouldSendWeeklyDigestMessage (same ISO week) and ShouldSendDailyDigestMessage
+		// (well under an hour elapsed) false — no need for a second user or settings.
+		resp, err := e.DoPluginAPIRequestWithHeaders(context.Background(), e.ServerClient, http.MethodGet, "/api/v0/bot/connect", "", nil)
+		require.NoError(t, err)
+		assert.Equal(t, http.StatusOK, resp.StatusCode)
+
+		// GetPostsSince is exclusive (server queries UpdateAt > since), so digestPost
+		// itself won't reappear here.
+		sincePosts, _, err := e.ServerClient.GetPostsSince(context.Background(), dmChannel.Id, digestPost.CreateAt, false)
+		require.NoError(t, err)
+		assert.Empty(t, sincePosts.Order, "expected no digest on the second immediate connect")
+	})
+}