diff --git a/src/log/syslog.rs b/src/log/syslog.rs
index 86eff0554..10df1fcd9 100644
--- a/src/log/syslog.rs
+++ b/src/log/syslog.rs
@@ -51,14 +51,20 @@ impl Write for SysLogWriter {
             if self.cursor + message.len() > LIMIT {
                 // floor_char_boundary is currently unstable
                 let mut truncate_boundary = LIMIT - self.cursor;
-                while !message.is_char_boundary(truncate_boundary) {
+                while truncate_boundary > 0 && !message.is_char_boundary(truncate_boundary) {
                     truncate_boundary -= 1;
                 }
 
+                // don't overzealously truncate log messages
                 truncate_boundary = message[..truncate_boundary]
                     .rfind(|c: char| c.is_ascii_whitespace())
                     .unwrap_or(truncate_boundary);
 
+                if truncate_boundary == 0 {
+                    // we failed to find a "nice" cut off point, abruptly cut off the msg
+                    truncate_boundary = LIMIT - self.cursor;
+                }
+
                 let left = &message[..truncate_boundary];
                 let right = &message[truncate_boundary..];
 
diff --git a/test-framework/e2e-tests/src/lib.rs b/test-framework/e2e-tests/src/lib.rs
index a9f98cbdf..3d9008f26 100644
--- a/test-framework/e2e-tests/src/lib.rs
+++ b/test-framework/e2e-tests/src/lib.rs
@@ -1,6 +1,7 @@
 #![cfg(test)]
 
 mod pty;
+mod regression;
 mod su;
 
 type Error = Box<dyn std::error::Error>;
diff --git a/test-framework/e2e-tests/src/regression.rs b/test-framework/e2e-tests/src/regression.rs
new file mode 100644
index 000000000..967aaf75a
--- /dev/null
+++ b/test-framework/e2e-tests/src/regression.rs
@@ -0,0 +1,17 @@
+use sudo_test::{Command, Env, TextFile};
+
+use crate::Result;
+
+#[test]
+fn syslog_writer_should_not_hang() -> Result<()> {
+    let env = Env(TextFile("ALL ALL=(ALL:ALL) NOPASSWD: ALL").chmod("644")).build()?;
+
+    let stdout = Command::new("sudo")
+        .args(["env", "CC=clang-18", "CXX=clang++-18", "FOO=\"........................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................................\"", "whoami"])
+        .output(&env)?
+        .stdout()?;
+
+    assert_eq!(stdout, "root");
+
+    Ok(())
+}