diff --git a/cli/src/invocation/cmd/sync.rs b/cli/src/invocation/cmd/sync.rs
index a042a5bf4..7a3708421 100644
--- a/cli/src/invocation/cmd/sync.rs
+++ b/cli/src/invocation/cmd/sync.rs
@@ -1,5 +1,5 @@
 use crate::settings::Settings;
-use taskchampion::{server::Server, Replica};
+use taskchampion::{server::Server, Error as TCError, Replica};
 use termcolor::WriteColor;
 
 pub(crate) fn execute<W: WriteColor>(
@@ -8,9 +8,32 @@ pub(crate) fn execute<W: WriteColor>(
     settings: &Settings,
     server: &mut Box<dyn Server>,
 ) -> Result<(), crate::Error> {
-    replica.sync(server, settings.avoid_snapshots)?;
-    writeln!(w, "sync complete.")?;
-    Ok(())
+    match replica.sync(server, settings.avoid_snapshots) {
+        Ok(()) => {
+            writeln!(w, "sync complete.")?;
+            Ok(())
+        }
+        Err(e) => match e.downcast() {
+            Ok(TCError::OutOfSync) => {
+                writeln!(w, "This replica cannot be synchronized with the server.")?;
+                writeln!(
+                    w,
+                    "It may be too old, or some other failure may have occurred."
+                )?;
+                writeln!(
+                    w,
+                    "To start fresh, remove the local task database and run `ta sync` again."
+                )?;
+                writeln!(
+                    w,
+                    "Note that doing so will lose any un-synchronized local changes."
+                )?;
+                Ok(())
+            }
+            Ok(e) => Err(e.into()),
+            Err(e) => Err(e.into()),
+        },
+    }
 }
 
 #[cfg(test)]
diff --git a/taskchampion/src/errors.rs b/taskchampion/src/errors.rs
index 44bad9881..3209b6ea9 100644
--- a/taskchampion/src/errors.rs
+++ b/taskchampion/src/errors.rs
@@ -4,6 +4,12 @@ use thiserror::Error;
 #[non_exhaustive]
 /// Errors returned from taskchampion operations
 pub enum Error {
+    /// A task-database-related error
     #[error("Task Database Error: {0}")]
     Database(String),
+    /// An error specifically indicating that the local replica cannot
+    /// be synchronized with the sever, due to being out of date or some
+    /// other irrecoverable error.
+    #[error("Local replica is out of sync with the server")]
+    OutOfSync,
 }
diff --git a/taskchampion/src/replica.rs b/taskchampion/src/replica.rs
index cc6338ceb..7afbc90a3 100644
--- a/taskchampion/src/replica.rs
+++ b/taskchampion/src/replica.rs
@@ -140,7 +140,7 @@ impl Replica {
     ) -> anyhow::Result<()> {
         self.taskdb
             .sync(server, avoid_snapshots)
-            .context("Failed to synchronize")?;
+            .context("Failed to synchronize with server")?;
         self.rebuild_working_set(false)
             .context("Failed to rebuild working set after sync")?;
         Ok(())
diff --git a/taskchampion/src/taskdb/sync.rs b/taskchampion/src/taskdb/sync.rs
index e77a5db66..7ce1d76ce 100644
--- a/taskchampion/src/taskdb/sync.rs
+++ b/taskchampion/src/taskdb/sync.rs
@@ -1,6 +1,7 @@
 use super::{ops, snapshot};
 use crate::server::{AddVersionResult, GetVersionResult, Server, SnapshotUrgency};
 use crate::storage::{Operation, StorageTxn};
+use crate::Error;
 use log::{info, trace, warn};
 use serde::{Deserialize, Serialize};
 use std::str;
@@ -97,7 +98,7 @@ pub(super) fn sync(
                 );
                 if let Some(requested) = requested_parent_version_id {
                     if parent_version_id == requested {
-                        anyhow::bail!("Server's task history has diverged from this replica");
+                        return Err(Error::OutOfSync.into());
                     }
                 }
                 requested_parent_version_id = Some(parent_version_id);