diff --git a/crates/spfs-cli/common/src/args.rs b/crates/spfs-cli/common/src/args.rs
index 7e81f9a74f..bce4e1bee2 100644
--- a/crates/spfs-cli/common/src/args.rs
+++ b/crates/spfs-cli/common/src/args.rs
@@ -7,7 +7,7 @@ use std::panic::catch_unwind;
 #[cfg(feature = "sentry")]
 use std::sync::Mutex;
 
-use miette::Error;
+use miette::{Error, IntoDiagnostic, Result, WrapErr};
 #[cfg(feature = "sentry")]
 use once_cell::sync::OnceCell;
 use spfs::io::Pluralize;
@@ -447,7 +447,12 @@ impl ExternalDataViewing {
                 "key".pluralize(num_keys),
                 keys.join(", ")
             );
-            println!("{}", serde_yaml::to_string(&data)?);
+            println!(
+                "{}",
+                serde_yaml::to_string(&data)
+                    .into_diagnostic()
+                    .wrap_err("Failed to generate yaml output")?
+            );
         } else if let Some(keys) = &self.get {
             tracing::debug!("--get these keys: {}", keys.join(", "));
             for key in keys.iter() {
diff --git a/crates/spfs-cli/main/src/cmd_run.rs b/crates/spfs-cli/main/src/cmd_run.rs
index badc3d0939..6eed8e117b 100644
--- a/crates/spfs-cli/main/src/cmd_run.rs
+++ b/crates/spfs-cli/main/src/cmd_run.rs
@@ -8,7 +8,7 @@ use std::io;
 use std::time::Instant;
 
 use clap::{ArgGroup, Args};
-use miette::{Context, Result};
+use miette::{miette, Context, IntoDiagnostic, Result};
 use spfs::runtime::KeyValuePair;
 use spfs::storage::FromConfig;
 use spfs::tracking::EnvSpec;
@@ -65,14 +65,17 @@ impl ExternalData {
                     // Treat '-' as "read from stdin"
                     Box::new(io::stdin())
                 } else {
-                    Box::new(std::fs::File::open(filename).with_context(|| {
-                        format!("Failed to open external data file: {filename:?}")
-                    })?)
+                    Box::new(
+                        std::fs::File::open(filename)
+                            .into_diagnostic()
+                            .wrap_err(format!("Failed to open external data file: {filename:?}"))?,
+                    )
                 };
             let external_data: BTreeMap<String, String> = serde_yaml::from_reader(reader)
-                .with_context(|| {
-                    format!("Failed to parse as external data key-value pairs: {filename:?}")
-                })?;
+                .into_diagnostic()
+                .wrap_err(format!(
+                    "Failed to parse as external data key-value pairs: {filename:?}"
+                ))?;
             data.extend(external_data);
         }
 
@@ -80,7 +83,8 @@ impl ExternalData {
             let pair = pair.trim();
             if pair.starts_with('{') {
                 let given: BTreeMap<String, String> = serde_yaml::from_str(pair)
-                    .context("--external-data value looked like yaml, but could not be parsed")?;
+                    .into_diagnostic()
+                    .wrap_err("--external-data value looked like yaml, but could not be parsed")?;
                 data.extend(given);
                 continue;
             }
@@ -89,7 +93,7 @@ impl ExternalData {
                 .split_once('=')
                 .or_else(|| pair.split_once(':'))
                 .ok_or_else(|| {
-                    anyhow!(
+                    miette!(
                         "Invalid option: -external-data {pair} (should be in the form name=value)"
                     )
                 })?;