diff --git a/Cargo.lock b/Cargo.lock
index 2c933485a..7c595bd65 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -2637,6 +2637,12 @@ dependencies = [
  "webpki 0.21.4",
 ]
 
+[[package]]
+name = "rustversion"
+version = "1.0.6"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f2cc38e8fa666e2de3c4aba7edeb5ffc5246c1c2ed0e3d17e560aeeba736b23f"
+
 [[package]]
 name = "ryu"
 version = "1.0.9"
@@ -2918,6 +2924,28 @@ version = "0.10.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "73473c0e59e6d5812c5dfe2a064a6444949f089e20eec9a2e5506596494e4623"
 
+[[package]]
+name = "strum"
+version = "0.24.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e96acfc1b70604b8b2f1ffa4c57e59176c7dbb05d556c71ecd2f5498a1dee7f8"
+dependencies = [
+ "strum_macros",
+]
+
+[[package]]
+name = "strum_macros"
+version = "0.24.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "6878079b17446e4d3eba6192bb0a2950d5b14f0ed8424b852310e5a94345d0ef"
+dependencies = [
+ "heck",
+ "proc-macro2",
+ "quote",
+ "rustversion",
+ "syn",
+]
+
 [[package]]
 name = "subtle"
 version = "2.4.1"
@@ -3410,6 +3438,7 @@ dependencies = [
  "derive_more",
  "futures",
  "once_cell",
+ "strum",
  "thiserror",
 ]
 
diff --git a/crates/tor-error/Cargo.toml b/crates/tor-error/Cargo.toml
index e66b6d31d..1b05b7b14 100644
--- a/crates/tor-error/Cargo.toml
+++ b/crates/tor-error/Cargo.toml
@@ -18,6 +18,7 @@ backtrace = { version = "0.3.39", optional = true }
 derive_more = "0.99"
 futures = "0.3"
 once_cell = "1"
+strum = { version = "0.24", features = ["derive"] }
 thiserror = "1"
 
 [dev-dependencies]
diff --git a/crates/tor-error/src/retriable.rs b/crates/tor-error/src/retriable.rs
index 9f68ca486..568252eb8 100644
--- a/crates/tor-error/src/retriable.rs
+++ b/crates/tor-error/src/retriable.rs
@@ -4,6 +4,7 @@ use std::{
     cmp::Ordering,
     time::{Duration, Instant},
 };
+use strum::EnumDiscriminants;
 
 /// A description of when an operation may be retried.
 ///
@@ -35,8 +36,12 @@ use std::{
 /// traffic to port 23 (telnet), we say that building a request for such a relay
 /// is not retriable, even though technically such a relay might appear in the
 /// next consensus.
-#[derive(Copy, Clone, Debug, Eq, PartialEq)]
+#[derive(Copy, Clone, Debug, Eq, PartialEq, EnumDiscriminants)]
 #[non_exhaustive]
+// We define a discriminant type so we can simplify loose_cmp.
+#[strum_discriminants(derive(Ord, PartialOrd))]
+// We don't want to expose RetryTimeDiscriminants.
+#[strum_discriminants(vis())]
 pub enum RetryTime {
     /// The operation can be retried immediately, and no delay is needed.
     ///
@@ -186,32 +191,70 @@ impl RetryTime {
     ///
     /// If you need an absolute comparison operator, convert to [`AbsRetryTime`] first.
     fn loose_cmp(&self, other: &Self) -> Ordering {
-        use Ordering::*;
+        use RetryTime as RT;
+
         match (self, other) {
-            // Immediate precedes everything.
-            (RetryTime::Immediate, RetryTime::Immediate) => Equal,
-            (RetryTime::Immediate, _) => Less,
-            (_, RetryTime::Immediate) => Greater,
+            // When we have the same type with an internal embedded duration or time,
+            // we compare based on the duration or time.
+            (RT::After(d1), RetryTime::After(d2)) => d1.cmp(d2),
+            (RT::At(t1), RetryTime::At(t2)) => t1.cmp(t2),
 
-            // When we have the same type, then we can compare based on actual
-            // times.
-            (RetryTime::AfterWaiting, RetryTime::AfterWaiting) => Equal,
-            (RetryTime::After(d1), RetryTime::After(d2)) => d1.cmp(d2),
-            (RetryTime::At(t1), RetryTime::At(t2)) => t1.cmp(t2),
-
-            // Otherwise: pretend AfterWaiting is shorter than After, is shorter
-            // than At.
-            (RetryTime::AfterWaiting, RetryTime::After(_)) => Less,
-            (RetryTime::AfterWaiting, RetryTime::At(_)) => Less,
-            (RetryTime::After(_), RetryTime::AfterWaiting) => Greater,
-            (RetryTime::After(_), RetryTime::At(_)) => Less,
-            (RetryTime::At(_), RetryTime::AfterWaiting) => Greater,
-            (RetryTime::At(_), RetryTime::After(_)) => Greater,
-
-            // Everything precedes Never.
-            (RetryTime::Never, RetryTime::Never) => Equal,
-            (RetryTime::Never, _) => Greater,
-            (_, RetryTime::Never) => Less,
+            // Otherwise, we compare based on discriminant type.
+            //
+            // This can't do a perfect "apples-to-apples" comparison for
+            // `AfterWaiting` vs `At` vs `After`, but at least it imposes a
+            // total order.
+            (a, b) => RetryTimeDiscriminants::from(a).cmp(&RetryTimeDiscriminants::from(b)),
+        }
+    }
+}
+
+#[cfg(test)]
+mod test {
+    use super::*;
+
+    #[test]
+    fn comparison() {
+        use RetryTime as RT;
+        let sec = Duration::from_secs(1);
+        let now = Instant::now();
+
+        let sorted = vec![
+            RT::Immediate,
+            RT::AfterWaiting,
+            RT::After(sec * 10),
+            RT::After(sec * 20),
+            RT::At(now),
+            RT::At(now + sec * 30),
+            RT::Never,
+        ];
+
+        // Verify that these objects are actually in loose-cmp sorted order.
+        for (i, a) in sorted.iter().enumerate() {
+            for (j, b) in sorted.iter().enumerate() {
+                assert_eq!(a.loose_cmp(b), i.cmp(&j));
+            }
+        }
+    }
+
+    #[test]
+    fn abs_comparison() {
+        use AbsRetryTime as ART;
+        let sec = Duration::from_secs(1);
+        let now = Instant::now();
+
+        let sorted = vec![
+            ART::Immediate,
+            ART::At(now),
+            ART::At(now + sec * 30),
+            ART::Never,
+        ];
+
+        // Verify that these objects are actually in loose-cmp sorted order.
+        for (i, a) in sorted.iter().enumerate() {
+            for (j, b) in sorted.iter().enumerate() {
+                assert_eq!(a.cmp(b), i.cmp(&j));
+            }
         }
     }
 }