diff --git a/src/agent/onefuzz-agent/src/tasks/coverage/libfuzzer_coverage.rs b/src/agent/onefuzz-agent/src/tasks/coverage/libfuzzer_coverage.rs
index 0b7f8762b..19edc58ad 100644
--- a/src/agent/onefuzz-agent/src/tasks/coverage/libfuzzer_coverage.rs
+++ b/src/agent/onefuzz-agent/src/tasks/coverage/libfuzzer_coverage.rs
@@ -36,7 +36,7 @@ use crate::tasks::{
     coverage::{recorder::CoverageRecorder, total::TotalCoverage},
     utils::default_bool_true,
 };
-use anyhow::Result;
+use anyhow::{Context, Result};
 use async_trait::async_trait;
 use futures::stream::StreamExt;
 use onefuzz::{
@@ -124,7 +124,9 @@ impl CoverageTask {
                 seen_inputs = true;
             }
 
-            fs::remove_dir_all(&dir.path).await?;
+            fs::remove_dir_all(&dir.path).await.with_context(|| {
+                format!("unable to remove readonly_inputs: {}", dir.path.display())
+            })?;
         }
 
         if seen_inputs {
@@ -154,7 +156,12 @@ impl CoverageTask {
         processor: &mut CoverageProcessor,
         corpus_dir: &SyncedDir,
     ) -> Result<bool> {
-        let mut corpus = fs::read_dir(&corpus_dir.path).await?;
+        let mut corpus = fs::read_dir(&corpus_dir.path).await.with_context(|| {
+            format!(
+                "unable to read corpus coverage directory: {}",
+                corpus_dir.path.display()
+            )
+        })?;
         let mut seen_inputs = false;
 
         while let Some(input) = corpus.next().await {
@@ -208,7 +215,12 @@ impl CoverageProcessor {
 
         if !self.module_totals.contains_key(&module) {
             let parent = &self.config.coverage.path.join("by-module");
-            fs::create_dir_all(parent).await?;
+            fs::create_dir_all(parent).await.with_context(|| {
+                format!(
+                    "unable to create by-module coverage directory: {}",
+                    parent.display()
+                )
+            })?;
             let module_total = parent.join(&module);
             let total = TotalCoverage::new(module_total);
             self.module_totals.insert(module.clone(), total);
@@ -226,7 +238,9 @@ impl CoverageProcessor {
 
         for file in &files {
             verbose!("checking {:?}", file);
-            let mut content = fs::read(file).await?;
+            let mut content = fs::read(file)
+                .await
+                .with_context(|| format!("unable to read module coverage: {}", file.display()))?;
             self.update_module_total(file, &content).await?;
             sum.append(&mut content);
         }
@@ -234,7 +248,9 @@ impl CoverageProcessor {
         let mut combined = path.as_os_str().to_owned();
         combined.push(".cov");
 
-        fs::write(&combined, sum).await?;
+        fs::write(&combined, sum)
+            .await
+            .with_context(|| format!("unable to write combined coverage file: {:?}", combined))?;
 
         Ok(combined.into())
     }
diff --git a/src/agent/onefuzz-agent/src/tasks/coverage/recorder.rs b/src/agent/onefuzz-agent/src/tasks/coverage/recorder.rs
index 1556e25e1..857ba191f 100644
--- a/src/agent/onefuzz-agent/src/tasks/coverage/recorder.rs
+++ b/src/agent/onefuzz-agent/src/tasks/coverage/recorder.rs
@@ -8,7 +8,7 @@ use std::{
     sync::Arc,
 };
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use onefuzz::{
     fs::{has_files, OwnedDir},
     sha256::digest_file,
@@ -47,7 +47,12 @@ impl CoverageRecorder {
             self.config.coverage.path.join("inputs").join(digest)
         };
 
-        fs::create_dir_all(&coverage_path).await?;
+        fs::create_dir_all(&coverage_path).await.with_context(|| {
+            format!(
+                "unable to create coverage path: {}",
+                coverage_path.display()
+            )
+        })?;
 
         let script = self.invoke_debugger_script(test_input, &coverage_path)?;
         let output = script.wait_with_output().await?;
@@ -77,7 +82,14 @@ impl CoverageRecorder {
         }
 
         if !has_files(&coverage_path).await? {
-            tokio::fs::remove_dir(&coverage_path).await?;
+            tokio::fs::remove_dir(&coverage_path)
+                .await
+                .with_context(|| {
+                    format!(
+                        "unable to remove coverage path: {}",
+                        coverage_path.display()
+                    )
+                })?;
             bail!("no coverage files for input: {}", test_input.display());
         }
 
diff --git a/src/agent/onefuzz-agent/src/tasks/fuzz/libfuzzer_fuzz.rs b/src/agent/onefuzz-agent/src/tasks/fuzz/libfuzzer_fuzz.rs
index 26a353643..29ffd8d53 100644
--- a/src/agent/onefuzz-agent/src/tasks/fuzz/libfuzzer_fuzz.rs
+++ b/src/agent/onefuzz-agent/src/tasks/fuzz/libfuzzer_fuzz.rs
@@ -2,7 +2,7 @@
 // Licensed under the MIT License.
 
 use crate::tasks::{config::CommonConfig, heartbeat::HeartbeatSender, utils::default_bool_true};
-use anyhow::Result;
+use anyhow::{Context, Result};
 use futures::{future::try_join_all, stream::StreamExt};
 use onefuzz::{
     fs::list_files,
@@ -120,7 +120,15 @@ impl LibFuzzerFuzzTask {
             let mut entries = tokio::fs::read_dir(local_input_dir.path()).await?;
             while let Some(Ok(entry)) = entries.next().await {
                 let destination_path = self.config.inputs.path.clone().join(entry.file_name());
-                tokio::fs::rename(entry.path(), destination_path).await?;
+                tokio::fs::rename(&entry.path(), &destination_path)
+                    .await
+                    .with_context(|| {
+                        format!(
+                            "unable to move crashing input into results directory: {} - {}?",
+                            entry.path().display(),
+                            destination_path.display()
+                        )
+                    })?;
             }
         }
     }
diff --git a/src/agent/onefuzz-agent/src/tasks/stats/afl.rs b/src/agent/onefuzz-agent/src/tasks/stats/afl.rs
index 4a2115767..194a25e71 100644
--- a/src/agent/onefuzz-agent/src/tasks/stats/afl.rs
+++ b/src/agent/onefuzz-agent/src/tasks/stats/afl.rs
@@ -1,13 +1,19 @@
 // Copyright (c) Microsoft Corporation.
 // Licensed under the MIT License.
 
-use anyhow::{Error, Result};
+use anyhow::{Context, Error, Result};
 use onefuzz::telemetry::EventData;
 use std::path::Path;
 use tokio::io::AsyncBufReadExt;
 
 pub async fn read_stats(output_path: impl AsRef<Path>) -> Result<Vec<EventData>, Error> {
-    let f = tokio::fs::File::open(output_path).await?;
+    let output_path = output_path.as_ref();
+    let f = tokio::fs::File::open(&output_path).await.with_context(|| {
+        format!(
+            "unable to open AFL stats for read: {}",
+            output_path.display()
+        )
+    })?;
     let mut stats = Vec::new();
 
     let reader = tokio::io::BufReader::new(f);
diff --git a/src/agent/onefuzz-supervisor/src/config.rs b/src/agent/onefuzz-supervisor/src/config.rs
index d235bbbd7..8d496cb97 100644
--- a/src/agent/onefuzz-supervisor/src/config.rs
+++ b/src/agent/onefuzz-supervisor/src/config.rs
@@ -1,7 +1,7 @@
 // Copyright (c) Microsoft Corporation.
 // Licensed under the MIT License.
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use onefuzz::{
     http::{is_auth_error_code, ResponseExt},
     jitter::delay_with_jitter,
@@ -83,7 +83,9 @@ impl StaticConfig {
     }
 
     pub fn from_file(config_path: impl AsRef<Path>) -> Result<Self> {
-        let data = std::fs::read(config_path)?;
+        let config_path = config_path.as_ref();
+        let data = std::fs::read(config_path)
+            .with_context(|| format!("unable to read config file: {}", config_path.display()))?;
         Self::new(&data)
     }
 
@@ -151,14 +153,18 @@ impl DynamicConfig {
     pub async fn save(&self) -> Result<()> {
         let path = Self::save_path()?;
         let data = serde_json::to_vec(&self)?;
-        fs::write(&path, &data).await?;
+        fs::write(&path, &data)
+            .await
+            .with_context(|| format!("unable to save dynamic config: {}", path.display()))?;
         info!("saved dynamic-config: {}", path.display());
         Ok(())
     }
 
     pub async fn load() -> Result<Self> {
         let path = Self::save_path()?;
-        let data = fs::read(&path).await?;
+        let data = fs::read(&path)
+            .await
+            .with_context(|| format!("unable to load dynamic config: {}", path.display()))?;
         let ctx: Self = serde_json::from_slice(&data)?;
         info!("loaded dynamic-config: {}", path.display());
         Ok(ctx)
diff --git a/src/agent/onefuzz-supervisor/src/done.rs b/src/agent/onefuzz-supervisor/src/done.rs
index 3f63e43ae..8c10fc988 100644
--- a/src/agent/onefuzz-supervisor/src/done.rs
+++ b/src/agent/onefuzz-supervisor/src/done.rs
@@ -4,12 +4,15 @@
 use std::fs::metadata;
 use std::path::PathBuf;
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use onefuzz::fs::onefuzz_root;
 use tokio::fs;
 
 pub async fn set_done_lock() -> Result<()> {
-    fs::write(done_path()?, "").await?;
+    let path = done_path()?;
+    fs::write(&path, "")
+        .await
+        .with_context(|| format!("unable to write done lock: {}", path.display()))?;
     Ok(())
 }
 
diff --git a/src/agent/onefuzz-supervisor/src/reboot.rs b/src/agent/onefuzz-supervisor/src/reboot.rs
index 518c4f16b..e0fa264f1 100644
--- a/src/agent/onefuzz-supervisor/src/reboot.rs
+++ b/src/agent/onefuzz-supervisor/src/reboot.rs
@@ -4,7 +4,7 @@
 use std::path::PathBuf;
 use std::process::Command;
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use downcast_rs::Downcast;
 use tokio::fs;
 
@@ -40,13 +40,14 @@ pub struct Reboot;
 
 impl Reboot {
     pub async fn save_context(&mut self, ctx: RebootContext) -> Result<()> {
-        info!(
-            "saving reboot context to: {}",
-            reboot_context_path()?.display()
-        );
+        let path = reboot_context_path()?;
+
+        info!("saving reboot context to: {}", path.display());
 
         let data = serde_json::to_vec(&ctx)?;
-        fs::write(reboot_context_path()?, &data).await?;
+        fs::write(&path, &data)
+            .await
+            .with_context(|| format!("unable to save reboot context: {}", path.display()))?;
 
         verbose!("reboot context saved");
 
@@ -72,7 +73,9 @@ impl Reboot {
         let data = data?;
         let ctx = serde_json::from_slice(&data)?;
 
-        fs::remove_file(&path).await?;
+        fs::remove_file(&path)
+            .await
+            .with_context(|| format!("unable to remove reboot context: {}", path.display()))?;
 
         info!("loaded reboot context");
         Ok(Some(ctx))
diff --git a/src/agent/onefuzz-supervisor/src/setup.rs b/src/agent/onefuzz-supervisor/src/setup.rs
index 519637c31..219a67277 100644
--- a/src/agent/onefuzz-supervisor/src/setup.rs
+++ b/src/agent/onefuzz-supervisor/src/setup.rs
@@ -4,7 +4,7 @@
 use std::path::{Path, PathBuf};
 use std::process::Stdio;
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use downcast_rs::Downcast;
 use onefuzz::az_copy;
 use onefuzz::process::Output;
@@ -48,7 +48,9 @@ impl SetupRunner {
             .join(setup_dir);
 
         // `azcopy sync` requires the local dir to exist.
-        fs::create_dir_all(&setup_dir).await?;
+        fs::create_dir_all(&setup_dir).await.with_context(|| {
+            format!("unable to create setup container: {}", setup_dir.display())
+        })?;
         az_copy::sync(setup_url.to_string(), &setup_dir, false).await?;
 
         verbose!(
@@ -106,8 +108,15 @@ async fn create_setup_symlink(setup_dir: &Path, work_unit: &WorkUnit) -> Result<
     use std::os::windows::fs::symlink_dir;
     use tokio::task::spawn_blocking;
 
-    fs::create_dir(&work_unit.working_dir()?).await?;
-    let task_setup_dir = work_unit.working_dir()?.join("setup");
+    let working_dir = work_unit.working_dir()?;
+
+    fs::create_dir(&working_dir).await.with_context(|| {
+        format!(
+            "unable to create working directory: {}",
+            working_dir.display()
+        )
+    })?;
+    let task_setup_dir = working_dir.join("setup");
 
     // Tokio does not ship async versions of the `std::fs::os` symlink
     // functions (unlike the Unix equivalents).
@@ -129,10 +138,27 @@ async fn create_setup_symlink(setup_dir: &Path, work_unit: &WorkUnit) -> Result<
 async fn create_setup_symlink(setup_dir: &Path, work_unit: &WorkUnit) -> Result<()> {
     use tokio::fs::os::unix::symlink;
 
-    tokio::fs::create_dir_all(work_unit.working_dir()?).await?;
+    let working_dir = work_unit.working_dir()?;
 
-    let task_setup_dir = work_unit.working_dir()?.join("setup");
-    symlink(&setup_dir, &task_setup_dir).await?;
+    tokio::fs::create_dir_all(&working_dir)
+        .await
+        .with_context(|| {
+            format!(
+                "unable to create working directory: {}",
+                working_dir.display()
+            )
+        })?;
+
+    let task_setup_dir = working_dir.join("setup");
+    symlink(&setup_dir, &task_setup_dir)
+        .await
+        .with_context(|| {
+            format!(
+                "unable to create symlink from {} to {}",
+                setup_dir.display(),
+                task_setup_dir.display()
+            )
+        })?;
 
     verbose!(
         "created symlink from {} to {}",
diff --git a/src/agent/onefuzz-supervisor/src/work.rs b/src/agent/onefuzz-supervisor/src/work.rs
index 199dbbff1..e66aef540 100644
--- a/src/agent/onefuzz-supervisor/src/work.rs
+++ b/src/agent/onefuzz-supervisor/src/work.rs
@@ -4,7 +4,7 @@
 use std::io::ErrorKind;
 use std::path::PathBuf;
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use downcast_rs::Downcast;
 use onefuzz::{blob::BlobContainerUrl, http::is_auth_error};
 use storage_queue::QueueClient;
@@ -63,7 +63,9 @@ impl WorkSet {
         info!("saving workset context: {}", path.display());
 
         let data = serde_json::to_vec(&self)?;
-        fs::write(path, &data).await?;
+        fs::write(&path, &data)
+            .await
+            .with_context(|| format!("unable to save WorkSet context: {}", path.display()))?;
 
         Ok(())
     }
diff --git a/src/agent/onefuzz-supervisor/src/worker.rs b/src/agent/onefuzz-supervisor/src/worker.rs
index 3f0890a68..a75ae223f 100644
--- a/src/agent/onefuzz-supervisor/src/worker.rs
+++ b/src/agent/onefuzz-supervisor/src/worker.rs
@@ -3,7 +3,7 @@
 
 use std::process::{Child, Command, Stdio};
 
-use anyhow::Result;
+use anyhow::{Context as AnyhowContext, Result};
 use downcast_rs::Downcast;
 use onefuzz::process::{ExitStatus, Output};
 use tokio::fs;
@@ -189,13 +189,20 @@ impl IWorkerRunner for WorkerRunner {
 
         verbose!("worker working dir = {}", working_dir.display());
 
-        fs::create_dir_all(&working_dir).await?;
+        fs::create_dir_all(&working_dir).await.with_context(|| {
+            format!(
+                "unable to create working directory: {}",
+                working_dir.display()
+            )
+        })?;
 
         verbose!("created worker working dir: {}", working_dir.display());
 
         let config_path = work.config_path()?;
 
-        fs::write(&config_path, work.config.expose_ref()).await?;
+        fs::write(&config_path, work.config.expose_ref())
+            .await
+            .with_context(|| format!("unable to save task config: {}", config_path.display()))?;
 
         verbose!(
             "wrote worker config to config_path = {}",
diff --git a/src/agent/onefuzz/src/fs.rs b/src/agent/onefuzz/src/fs.rs
index ceb8ef876..099242f59 100644
--- a/src/agent/onefuzz/src/fs.rs
+++ b/src/agent/onefuzz/src/fs.rs
@@ -1,7 +1,7 @@
 // Copyright (c) Microsoft Corporation.
 // Licensed under the MIT License.
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use futures::stream::StreamExt;
 use std::path::{Path, PathBuf};
 #[cfg(target_os = "linux")]
@@ -25,13 +25,19 @@ pub fn onefuzz_etc() -> Result<PathBuf> {
 }
 
 pub async fn has_files(path: impl AsRef<Path>) -> Result<bool> {
-    let mut paths = fs::read_dir(&path).await?;
+    let path = path.as_ref();
+    let mut paths = fs::read_dir(&path)
+        .await
+        .with_context(|| format!("unable to check if directory has files: {}", path.display()))?;
     let result = paths.next_entry().await?.is_some();
     Ok(result)
 }
 
 pub async fn list_files(path: impl AsRef<Path>) -> Result<Vec<PathBuf>> {
-    let paths = fs::read_dir(&path).await?;
+    let path = path.as_ref();
+    let paths = fs::read_dir(&path)
+        .await
+        .with_context(|| format!("unable to list files: {}", path.display()))?;
 
     let mut files = paths
         .filter_map(|x| async {
@@ -106,8 +112,12 @@ pub async fn write_file(path: impl AsRef<Path>, content: &str) -> Result<()> {
     let parent = path
         .parent()
         .ok_or_else(|| format_err!("no parent for: {}", path.display()))?;
-    fs::create_dir_all(parent).await?;
-    fs::write(path, content).await?;
+    fs::create_dir_all(parent)
+        .await
+        .with_context(|| format!("unable to create nested path: {}", parent.display()))?;
+    fs::write(path, content)
+        .await
+        .with_context(|| format!("unable to write file: {}", path.display()))?;
     Ok(())
 }
 
@@ -115,10 +125,14 @@ pub async fn reset_dir(dir: impl AsRef<Path>) -> Result<()> {
     let dir = dir.as_ref();
 
     if exists(dir).await? {
-        fs::remove_dir_all(dir).await?;
+        fs::remove_dir_all(dir).await.with_context(|| {
+            format!("unable to remove directory and contents: {}", dir.display())
+        })?;
     }
 
-    fs::create_dir_all(dir).await?;
+    fs::create_dir_all(dir)
+        .await
+        .with_context(|| format!("unable to create directory: {}", dir.display()))?;
 
     Ok(())
 }
@@ -143,7 +157,9 @@ impl OwnedDir {
     }
 
     pub async fn create_if_missing(&self) -> Result<()> {
-        fs::create_dir_all(self.path()).await?;
+        fs::create_dir_all(self.path())
+            .await
+            .with_context(|| format!("unable to create directory: {}", self.path().display()))?;
         Ok(())
     }
 
diff --git a/src/agent/onefuzz/src/machine_id.rs b/src/agent/onefuzz/src/machine_id.rs
index 341204087..3e3a4ca1c 100644
--- a/src/agent/onefuzz/src/machine_id.rs
+++ b/src/agent/onefuzz/src/machine_id.rs
@@ -2,8 +2,9 @@
 // Licensed under the MIT License.
 
 use crate::fs::{onefuzz_etc, write_file};
-use anyhow::Result;
+use anyhow::{Context, Result};
 use reqwest_retry::SendRetry;
+use std::path::Path;
 use std::time::Duration;
 use tokio::fs;
 use uuid::Uuid;
@@ -83,7 +84,10 @@ pub async fn get_scaleset_name() -> Result<Option<String>> {
 
 #[cfg(target_os = "linux")]
 pub async fn get_os_machine_id() -> Result<Uuid> {
-    let contents = fs::read_to_string("/etc/machine-id").await?;
+    let path = Path::new("/etc/machine-id");
+    let contents = fs::read_to_string(&path)
+        .await
+        .with_context(|| format!("unable to read machine_id: {}", path.display()))?;
     let uuid = Uuid::parse_str(contents.trim())?;
     Ok(uuid)
 }
diff --git a/src/agent/onefuzz/src/sha256.rs b/src/agent/onefuzz/src/sha256.rs
index 8397f6581..37059746c 100644
--- a/src/agent/onefuzz/src/sha256.rs
+++ b/src/agent/onefuzz/src/sha256.rs
@@ -3,7 +3,7 @@
 
 use std::path::Path;
 
-use anyhow::Result;
+use anyhow::{Context, Result};
 use sha2::{Digest, Sha256};
 use tokio::fs;
 
@@ -22,7 +22,10 @@ pub fn digest_iter(data: impl IntoIterator<Item = impl AsRef<[u8]>>) -> String {
 }
 
 pub async fn digest_file(file: impl AsRef<Path>) -> Result<String> {
-    let data = fs::read(file).await?;
+    let file = file.as_ref();
+    let data = fs::read(file)
+        .await
+        .with_context(|| format!("unable to read file to generate digest: {}", file.display()))?;
 
     Ok(hex::encode(Sha256::digest(&data)))
 }
diff --git a/src/agent/onefuzz/src/syncdir.rs b/src/agent/onefuzz/src/syncdir.rs
index e6c308dc4..3a41104cd 100644
--- a/src/agent/onefuzz/src/syncdir.rs
+++ b/src/agent/onefuzz/src/syncdir.rs
@@ -9,7 +9,7 @@ use crate::{
     telemetry::{Event, EventData},
     uploader::BlobUploader,
 };
-use anyhow::Result;
+use anyhow::{Context, Result};
 use futures::stream::StreamExt;
 use std::{path::PathBuf, str, time::Duration};
 use tokio::fs;
@@ -55,7 +55,9 @@ impl SyncedDir {
                     anyhow::bail!("File with name '{}' already exists", self.path.display());
                 }
             }
-            Err(_) => fs::create_dir(&self.path).await.map_err(|e| e.into()),
+            Err(_) => fs::create_dir(&self.path).await.with_context(|| {
+                format!("unable to create local SyncedDir: {}", self.path.display())
+            }),
         }
     }