diff --git a/internal/client/github.go b/internal/client/github.go
index a4172818a..b309a152f 100644
--- a/internal/client/github.go
+++ b/internal/client/github.go
@@ -75,8 +75,15 @@ func (c *githubClient) checkRateLimit(ctx *context.Context) {
 		return
 	}
 	sleep := limits.Core.Reset.UTC().Sub(time.Now().UTC())
+	if sleep <= 0 {
+		// it seems that sometimes, after the rate limit just reset, it might
+		// still get <100 remaining and a reset time in the past... in such
+		// cases we can probably sleep a bit more before trying again...
+		sleep = 15 * time.Second
+	}
 	log.Warnf("token too close to rate limiting, will sleep for %s before continuing...", sleep)
 	time.Sleep(sleep)
+	c.checkRateLimit(ctx)
 }
 
 func (c *githubClient) GenerateReleaseNotes(ctx *context.Context, repo Repo, prev, current string) (string, error) {
diff --git a/internal/client/github_test.go b/internal/client/github_test.go
index 58b406557..fa1a8f0d3 100644
--- a/internal/client/github_test.go
+++ b/internal/client/github_test.go
@@ -8,6 +8,7 @@ import (
 	"net/http"
 	"net/http/httptest"
 	"os"
+	"sync/atomic"
 	"testing"
 	"text/template"
 	"time"
@@ -821,12 +822,21 @@ func TestGitHubCreateFileFeatureBranchDoesNotExist(t *testing.T) {
 func TestCheckRateLimit(t *testing.T) {
 	now := time.Now().UTC()
 	reset := now.Add(1392 * time.Millisecond)
+	var first atomic.Bool
 	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
 		defer r.Body.Close()
 		if r.URL.Path == "/rate_limit" {
 			w.WriteHeader(http.StatusOK)
 			resetstr, _ := github.Timestamp{Time: reset}.MarshalJSON()
+			if first.Load() {
+				// second time asking for the rate limit
+				fmt.Fprintf(w, `{"resources":{"core":{"remaining":138,"reset":%s}}}`, string(resetstr))
+				return
+			}
+
+			// first time asking for the rate limit
 			fmt.Fprintf(w, `{"resources":{"core":{"remaining":98,"reset":%s}}}`, string(resetstr))
+			first.Store(true)
 			return
 		}
 		t.Error("unhandled request: " + r.Method + " " + r.URL.Path)