diff --git a/src/rp2_common/pico_time_adapter/include/pico/time_adapter.h b/src/rp2_common/pico_time_adapter/include/pico/time_adapter.h
index bc9caf1ad..639e91498 100644
--- a/src/rp2_common/pico_time_adapter/include/pico/time_adapter.h
+++ b/src/rp2_common/pico_time_adapter/include/pico/time_adapter.h
@@ -55,9 +55,9 @@ static inline void ta_set_timeout(alarm_pool_timer_t *timer, uint alarm_num, int
 }
 
 static inline bool ta_wakes_up_on_or_before(alarm_pool_timer_t *timer, uint alarm_num, int64_t target) {
-    uint32_t current = timer_time_us_32(timer_hw_from_timer(timer));
-    uint32_t time_til_target = (uint32_t) target - current;
-    uint32_t time_til_alarm = timer_hw_from_timer(timer)->alarm[alarm_num] - current;
+    int64_t current = (int64_t)timer_time_us_64(timer_hw_from_timer(timer));
+    int64_t time_til_target = target - current;
+    uint32_t time_til_alarm = timer_hw_from_timer(timer)->alarm[alarm_num] - (uint32_t)current;
     return time_til_alarm <= time_til_target;
 }
 
diff --git a/test/pico_time_test/pico_time_test.c b/test/pico_time_test/pico_time_test.c
index 8092abbef..5ce013df5 100644
--- a/test/pico_time_test/pico_time_test.c
+++ b/test/pico_time_test/pico_time_test.c
@@ -76,6 +76,7 @@ int issue_195_test(void);
 int issue_1812_test(void);
 int issue_1953_test(void);
 int issue_2118_test(void);
+int issue_2186_test(void);
 
 int main() {
     setup_default_uart();
@@ -250,6 +251,8 @@ int main() {
 
     issue_2118_test();
 
+    issue_2186_test();
+
     PICOTEST_END_TEST();
 }
 
@@ -311,8 +314,8 @@ int issue_1953_test(void) {
     repeating_timer_t timer1;
     repeating_timer_t timer2;
 
-    assert(add_repeating_timer_us(10, timer_callback_issue_1953, NULL, &timer1));
-    assert(add_repeating_timer_us(100, timer_callback_issue_1953, NULL, &timer2));
+    hard_assert(add_repeating_timer_us(10, timer_callback_issue_1953, NULL, &timer1));
+    hard_assert(add_repeating_timer_us(100, timer_callback_issue_1953, NULL, &timer2));
 
     int iterations = 0;
     while(iterations < 100) {
@@ -364,3 +367,13 @@ int issue_2118_test(void) {
     PICOTEST_END_SECTION();
     return 0;
 }
+
+int issue_2186_test(void) {
+    PICOTEST_START_SECTION("Issue #2186 defect - ta_wakes_up_on_or_before");
+
+    hard_assert(best_effort_wfe_or_timeout(get_absolute_time() - 1));
+    hard_assert(best_effort_wfe_or_timeout(get_absolute_time() - 1)); // this will lockup without the fix - wfe which never happens
+
+    PICOTEST_END_SECTION();
+    return 0;
+}