diff --git a/pkg/cli/cmd/sync/sync.go b/pkg/cli/cmd/sync/sync.go
index 1e4a792c..de0739fe 100644
--- a/pkg/cli/cmd/sync/sync.go
+++ b/pkg/cli/cmd/sync/sync.go
@@ -631,7 +631,8 @@ func stepSync(ctx context.DnoteCtx, tx *database.DB, afterUSN int) error {
 func sendBooks(ctx context.DnoteCtx, tx *database.DB) (bool, error) {
 	isBehind := false
 
-	rows, err := tx.Query("SELECT uuid, label, usn, deleted FROM books WHERE dirty")
+	// send deleted books first to allow users to remain within the plan limit
+	rows, err := tx.Query("SELECT uuid, label, usn, deleted FROM books WHERE dirty ORDER BY deleted DESC")
 	if err != nil {
 		return isBehind, errors.Wrap(err, "getting syncable books")
 	}
diff --git a/pkg/server/handlers/routes.go b/pkg/server/handlers/routes.go
index 198b6640..badf7198 100644
--- a/pkg/server/handlers/routes.go
+++ b/pkg/server/handlers/routes.go
@@ -399,7 +399,7 @@ func NewRouter(app *App) (*mux.Router, error) {
 		{"OPTIONS", "/v3/books", cors(app.BooksOptions), true},
 		{"GET", "/v3/books", cors(app.auth(app.GetBooks, nil)), true},
 		{"GET", "/v3/books/{bookUUID}", cors(app.auth(app.GetBook, nil)), true},
-		{"POST", "/v3/books", cors(app.auth(app.CreateBook, &checkPlanLimit)), false},
+		{"POST", "/v3/books", cors(app.auth(app.CreateBook, nil)), false},
 		{"PATCH", "/v3/books/{bookUUID}", cors(app.auth(app.UpdateBook, &checkPlanLimit)), false},
 		{"DELETE", "/v3/books/{bookUUID}", cors(app.auth(app.DeleteBook, nil)), false},
 		{"OPTIONS", "/v3/notes", cors(app.NotesOptions), true},
diff --git a/pkg/server/handlers/v3_books.go b/pkg/server/handlers/v3_books.go
index 84d5dd76..f58c2bf2 100644
--- a/pkg/server/handlers/v3_books.go
+++ b/pkg/server/handlers/v3_books.go
@@ -27,6 +27,7 @@ import (
 	"github.com/dnote/dnote/pkg/server/database"
 	"github.com/dnote/dnote/pkg/server/helpers"
 	"github.com/dnote/dnote/pkg/server/operations"
+	"github.com/dnote/dnote/pkg/server/permissions"
 	"github.com/dnote/dnote/pkg/server/presenters"
 	"github.com/gorilla/mux"
 	"github.com/jinzhu/gorm"
@@ -71,9 +72,19 @@ func (a *App) CreateBook(w http.ResponseWriter, r *http.Request) {
 	}
 
 	var book database.Book
-	conn := a.DB.Model(database.Book{}).Where("user_id = ? AND label = ?", user.ID, params.Name).First(&book)
+	conn := a.DB.Debug().Model(database.Book{}).Where("user_id = ? AND label = ?", user.ID, params.Name).First(&book)
 
 	if conn.RecordNotFound() {
+		allowed, err := permissions.CanCreateBook(a.DB, user)
+		if err != nil {
+			HandleError(w, "checking plan threshold", err, http.StatusInternalServerError)
+			return
+		}
+		if !allowed {
+			a.respondPlanLimitExceeded(w)
+			return
+		}
+
 		b, err := operations.CreateBook(a.DB, user, a.Clock, params.Name)
 		if err != nil {
 			HandleError(w, "inserting book", err, http.StatusInternalServerError)
diff --git a/pkg/server/permissions/plan.go b/pkg/server/permissions/plan.go
index c3430735..88565e0f 100644
--- a/pkg/server/permissions/plan.go
+++ b/pkg/server/permissions/plan.go
@@ -18,9 +18,23 @@ func CheckPlanAllowance(db *gorm.DB, user database.User) (bool, error) {
 		return false, errors.Wrap(err, "checking plan threshold")
 	}
 
-	if bookCount >= 5 {
+	if bookCount > 5 {
 		return false, nil
 	}
 
 	return true, nil
 }
+
+// CanCreateBook checks if the given user can create a book
+func CanCreateBook(db *gorm.DB, user database.User) (bool, error) {
+	if user.Cloud {
+		return true, nil
+	}
+
+	var bookCount int
+	if err := db.Model(database.Book{}).Where("user_id = ? AND NOT deleted", user.ID).Count(&bookCount).Error; err != nil {
+		return false, errors.Wrap(err, "checking plan threshold")
+	}
+
+	return bookCount < 5, nil
+}