diff --git a/library/std/src/sys/pal/hermit/time.rs b/library/std/src/sys/pal/hermit/time.rs
index 89a427ab88ba9..978bd45114e1a 100644
--- a/library/std/src/sys/pal/hermit/time.rs
+++ b/library/std/src/sys/pal/hermit/time.rs
@@ -28,7 +28,7 @@ impl Timespec {
     #[rustc_const_unstable(feature = "const_system_time", issue = "144517")]
     const fn sub_timespec(&self, other: &Timespec) -> Result<Duration, Duration> {
         // FIXME: const PartialOrd
-        let mut cmp = self.t.tv_sec - other.t.tv_sec;
+        let mut cmp = self.t.tv_sec.saturating_sub(other.t.tv_sec);
         if cmp == 0 {
             cmp = self.t.tv_nsec as i64 - other.t.tv_nsec as i64;
         }
@@ -36,12 +36,12 @@ impl Timespec {
         if cmp >= 0 {
             Ok(if self.t.tv_nsec >= other.t.tv_nsec {
                 Duration::new(
-                    (self.t.tv_sec - other.t.tv_sec) as u64,
+                    self.t.tv_sec.wrapping_sub(other.t.tv_sec) as u64,
                     (self.t.tv_nsec - other.t.tv_nsec) as u32,
                 )
             } else {
                 Duration::new(
-                    (self.t.tv_sec - 1 - other.t.tv_sec) as u64,
+                    self.t.tv_sec.wrapping_sub(other.t.tv_sec) as u64 - 1_u64,
                     (self.t.tv_nsec + NSEC_PER_SEC - other.t.tv_nsec) as u32,
                 )
             })
diff --git a/library/std/src/sys/pal/uefi/time.rs b/library/std/src/sys/pal/uefi/time.rs
index 36ce3f7ef962e..91dcc2211aa9e 100644
--- a/library/std/src/sys/pal/uefi/time.rs
+++ b/library/std/src/sys/pal/uefi/time.rs
@@ -95,7 +95,7 @@ impl SystemTime {
 
         // Check if can be represented in UEFI
         // FIXME: const PartialOrd
-        let mut cmp = temp.as_secs() - MAX_UEFI_TIME.0.as_secs();
+        let mut cmp = temp.as_secs().saturating_sub(MAX_UEFI_TIME.0.as_secs());
         if cmp == 0 {
             cmp = temp.subsec_nanos() as u64 - MAX_UEFI_TIME.0.subsec_nanos() as u64;
         }
diff --git a/library/std/src/sys/pal/unix/time.rs b/library/std/src/sys/pal/unix/time.rs
index 328fe0bc9603f..6956deca6d35e 100644
--- a/library/std/src/sys/pal/unix/time.rs
+++ b/library/std/src/sys/pal/unix/time.rs
@@ -139,7 +139,7 @@ impl Timespec {
     #[rustc_const_unstable(feature = "const_system_time", issue = "144517")]
     pub const fn sub_timespec(&self, other: &Timespec) -> Result<Duration, Duration> {
         // FIXME: const PartialOrd
-        let mut cmp = self.tv_sec - other.tv_sec;
+        let mut cmp = self.tv_sec.saturating_sub(other.tv_sec);
         if cmp == 0 {
             cmp = self.tv_nsec.as_inner() as i64 - other.tv_nsec.as_inner() as i64;
         }
@@ -160,12 +160,12 @@ impl Timespec {
             // directly expresses the lower-cost behavior we want from it.
             let (secs, nsec) = if self.tv_nsec.as_inner() >= other.tv_nsec.as_inner() {
                 (
-                    (self.tv_sec - other.tv_sec) as u64,
+                    self.tv_sec.wrapping_sub(other.tv_sec) as u64,
                     self.tv_nsec.as_inner() - other.tv_nsec.as_inner(),
                 )
             } else {
                 (
-                    (self.tv_sec - other.tv_sec - 1) as u64,
+                    self.tv_sec.wrapping_sub(other.tv_sec) as u64 - 1_u64,
                     self.tv_nsec.as_inner() + (NSEC_PER_SEC as u32) - other.tv_nsec.as_inner(),
                 )
             };
diff --git a/library/std/tests/time.rs b/library/std/tests/time.rs
index 40709eae37cfc..e8aee25f6de43 100644
--- a/library/std/tests/time.rs
+++ b/library/std/tests/time.rs
@@ -227,3 +227,29 @@ fn big_math() {
     check(instant.checked_add(Duration::from_secs(100)), Instant::checked_sub);
     check(instant.checked_add(Duration::from_secs(i64::MAX as _)), Instant::checked_sub);
 }
+
+#[test]
+#[cfg(unix)]
+fn system_time_extreme_values_regression() {
+    // Test for regression in SystemTime comparison with extreme values
+    // This test covers the bug introduced in PR #144519 where integer overflow
+    // in the comparison logic caused incorrect results when dealing with times
+    // near i64::MIN and i64::MAX.
+    //
+    // This is the exact test case from GitHub issue #146228
+    let t = SystemTime::UNIX_EPOCH;
+    let early = t - (Duration::from_secs(i64::MAX as u64 + 1));
+    let later = t + (Duration::from_secs(i64::MAX as u64) + Duration::from_nanos(999_999_999));
+
+    // This should succeed and not return a SystemTimeError due to incorrect comparison overflow
+    let delta =
+        later.duration_since(early).expect("duration_since should work with extreme values");
+
+    // Verify that the delta calculation is reasonable
+    // early is at approximately -i64::MAX-1 seconds from epoch
+    // later is at approximately i64::MAX seconds + 999_999_999 nanoseconds from epoch
+    // So delta should be approximately (i64::MAX + i64::MAX + 1) seconds + 999_999_999 nanoseconds
+    let expected_secs = (i64::MAX as u64) * 2 + 1;
+    let expected = Duration::new(expected_secs, 999_999_999);
+    assert_eq!(delta, expected, "Duration calculation should be correct for extreme values");
+}