diff --git a/src/internal.c b/src/internal.c
index 9f6693882..a586650a8 100644
--- a/src/internal.c
+++ b/src/internal.c
@@ -15414,23 +15414,24 @@ int wolfSSL_DtlsUpdateWindow(word16 cur_hi, word32 cur_lo,
         else {
             curLT = cur_hi < *next_hi;
             if (curLT) {
-                if (cur_lo > (word32)(0 - DTLS_SEQ_BITS) &&
-                        *next_lo < DTLS_SEQ_BITS) {
-                    diff = *next_lo - cur_lo;
+                if (*next_lo < DTLS_SEQ_BITS &&
+                        cur_lo >= (((word32)0xFFFFFFFF) - DTLS_SEQ_BITS)) {
+                    /* diff here can still result in a difference that can not
+                     * be stored in the window. The index is checked against
+                     * WOLFSSL_DTLS_WINDOW_WORDS later. */
+                    diff = *next_lo + ((word32)0xFFFFFFFF - cur_lo) + 1;
                 }
                 else {
-                    _DtlsUpdateWindowGTSeq(0, window);
-                    *next_lo = cur_lo + 1;
-                    if (*next_lo == 0)
-                        *next_hi = cur_hi + 1;
-                    else
-                        *next_hi = cur_hi;
+                    /* Too far back to update */
                     return 1;
                 }
             }
             else {
-                if (*next_lo > (word32)(0 - DTLS_SEQ_BITS) &&
+                if (*next_lo >= (((word32)0xFFFFFFFF) - DTLS_SEQ_BITS) &&
                         cur_lo < DTLS_SEQ_BITS) {
+                    /* diff here can still result in a difference that can not
+                     * be stored in the window. The index is checked against
+                     * WOLFSSL_DTLS_WINDOW_WORDS later. */
                     diff = cur_lo - *next_lo;
                 }
                 else {
diff --git a/tests/api.c b/tests/api.c
index d54fd3cc4..a267d9610 100644
--- a/tests/api.c
+++ b/tests/api.c
@@ -55621,10 +55621,16 @@ static void test_wolfSSL_DtlsUpdateWindow(void)
     DUW_TEST(2, 29, next_hi, next_lo, window, 2, 30, 0, 0x64000015);
     DUW_TEST(2, 33, next_hi, next_lo, window, 2, 34, 6, 0x40000151);
     DUW_TEST(2, 60, next_hi, next_lo, window, 2, 61, 0x3200000A, 0x88000001);
+    DUW_TEST(1, 0xFFFFFFF0, next_hi, next_lo, window, 2, 61, 0x3200000A, 0x88000001);
     DUW_TEST(2, 0xFFFFFFFD, next_hi, next_lo, window, 2, 0xFFFFFFFE, 0, 0x01);
     DUW_TEST(3, 1, next_hi, next_lo, window, 3, 2, 0, 0x11);
     DUW_TEST(99, 66, next_hi, next_lo, window, 99, 67, 0, 0x01);
+    DUW_TEST(50, 66, next_hi, next_lo, window, 99, 67, 0, 0x01);
     DUW_TEST(100, 68, next_hi, next_lo, window, 100, 69, 0, 0x01);
+    DUW_TEST(99, 50, next_hi, next_lo, window, 100, 69, 0, 0x01);
+    DUW_TEST(99, 0xFFFFFFFF, next_hi, next_lo, window, 100, 69, 0, 0x01);
+    DUW_TEST(150, 0xFFFFFFFF, next_hi, next_lo, window, 151, 0, 0, 0x01);
+    DUW_TEST(152, 0xFFFFFFFF, next_hi, next_lo, window, 153, 0, 0, 0x01);
 
     printf(resultFmt, passed);
 }