diff --git a/Cargo.lock b/Cargo.lock
index 392ff5ef46..cd16ac1b7e 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -1532,9 +1532,9 @@ dependencies = [
 
 [[package]]
 name = "deno_core"
-version = "0.330.0"
+version = "0.331.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "fd38bbbd68ed873165ccb630322704b44140d3a8c8d50f898beac4d1a8a3358c"
+checksum = "ce2d1779358cad2bc56d71176298767be628d707bb75585f6f8a4be2da8ccda1"
 dependencies = [
  "anyhow",
  "az",
@@ -1658,9 +1658,9 @@ dependencies = [
 
 [[package]]
 name = "deno_error"
-version = "0.5.3"
+version = "0.5.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c4da6a58de6932a96f84e133c072fd3b525966ee122a71f3efd48bbff2eed5ac"
+checksum = "9c23dbc46d5804814b08b4675838f9884e3a52916987ec5105af36d42f9911b5"
 dependencies = [
  "deno_error_macro",
  "libc",
@@ -1672,9 +1672,9 @@ dependencies = [
 
 [[package]]
 name = "deno_error_macro"
-version = "0.5.3"
+version = "0.5.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "46351dff93aed2039407c91e2ded2a5591e42d2795ab3d111288625bb710d3d2"
+checksum = "babccedee31ce7e57c3e6dff2cb3ab8d68c49d0df8222fe0d11d628e65192790"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -2151,9 +2151,9 @@ dependencies = [
 
 [[package]]
 name = "deno_ops"
-version = "0.206.0"
+version = "0.207.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4c25ffa9d088ea00748dbef870bba110ac22ebf8cf7b2e9eb288409c5d852af3"
+checksum = "96f000a21f6969b4c945bc8e9e785aa439f11ca4fd3fbddcd5bebc102167eb37"
 dependencies = [
  "indexmap 2.3.0",
  "proc-macro-rules",
@@ -6947,9 +6947,9 @@ dependencies = [
 
 [[package]]
 name = "serde_v8"
-version = "0.239.0"
+version = "0.240.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3caa6d882827148e5d9052d9d8d6d1c9d6ad426ed00cab46cafb8c07a0e7126a"
+checksum = "cd0494d74c40ab94f53a19485de359ea6a55f05341b817b93440b673c1ce8ec6"
 dependencies = [
  "deno_error",
  "num-bigint",
diff --git a/Cargo.toml b/Cargo.toml
index 42c2970e05..83d4a8398a 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -49,7 +49,7 @@ repository = "https://github.com/denoland/deno"
 
 [workspace.dependencies]
 deno_ast = { version = "=0.44.0", features = ["transpiling"] }
-deno_core = { version = "0.330.0" }
+deno_core = { version = "0.331.0" }
 
 deno_bench_util = { version = "0.180.0", path = "./bench_util" }
 deno_config = { version = "=0.45.0", features = ["workspace", "sync"] }
@@ -123,7 +123,7 @@ dashmap = "5.5.3"
 data-encoding = "2.3.3"
 data-url = "=0.3.1"
 deno_cache_dir = "=0.16.0"
-deno_error = "=0.5.3"
+deno_error = "=0.5.5"
 deno_package_json = { version = "0.4.0", default-features = false }
 deno_unsync = "0.4.2"
 dlopen2 = "0.6.1"
diff --git a/cli/args/lockfile.rs b/cli/args/lockfile.rs
index 976992aac8..5fa6a49c43 100644
--- a/cli/args/lockfile.rs
+++ b/cli/args/lockfile.rs
@@ -61,11 +61,13 @@ impl<'a, T> std::ops::DerefMut for Guard<'a, T> {
 }
 
 #[derive(Debug, thiserror::Error, deno_error::JsError)]
-#[error("Failed writing lockfile")]
-#[class(inherit)]
-struct AtomicWriteFileWithRetriesError {
-  #[source]
-  source: std::io::Error,
+pub enum AtomicWriteFileWithRetriesError {
+  #[class(inherit)]
+  #[error(transparent)]
+  Changed(JsErrorBox),
+  #[class(inherit)]
+  #[error("Failed writing lockfile")]
+  Io(#[source] std::io::Error),
 }
 
 impl CliLockfile {
@@ -87,12 +89,16 @@ impl CliLockfile {
     self.lockfile.lock().overwrite
   }
 
-  pub fn write_if_changed(&self) -> Result<(), JsErrorBox> {
+  pub fn write_if_changed(
+    &self,
+  ) -> Result<(), AtomicWriteFileWithRetriesError> {
     if self.skip_write {
       return Ok(());
     }
 
-    self.error_if_changed()?;
+    self
+      .error_if_changed()
+      .map_err(AtomicWriteFileWithRetriesError::Changed)?;
     let mut lockfile = self.lockfile.lock();
     let Some(bytes) = lockfile.resolve_write_bytes() else {
       return Ok(()); // nothing to do
@@ -105,9 +111,7 @@ impl CliLockfile {
       &bytes,
       cache::CACHE_PERM,
     )
-    .map_err(|source| {
-      JsErrorBox::from_err(AtomicWriteFileWithRetriesError { source })
-    })?;
+    .map_err(AtomicWriteFileWithRetriesError::Io)?;
     lockfile.has_content_changed = false;
     Ok(())
   }
diff --git a/cli/args/mod.rs b/cli/args/mod.rs
index f77eedc594..46ada5440f 100644
--- a/cli/args/mod.rs
+++ b/cli/args/mod.rs
@@ -82,6 +82,7 @@ use deno_terminal::colors;
 use dotenvy::from_filename;
 pub use flags::*;
 use import_map::resolve_import_map_value_from_specifier;
+pub use lockfile::AtomicWriteFileWithRetriesError;
 pub use lockfile::CliLockfile;
 pub use lockfile::CliLockfileReadFromPathOptions;
 use once_cell::sync::Lazy;
diff --git a/cli/emit.rs b/cli/emit.rs
index 69ac8323bb..f928591eaf 100644
--- a/cli/emit.rs
+++ b/cli/emit.rs
@@ -112,9 +112,9 @@ impl Emitter {
     &self,
     specifier: &ModuleSpecifier,
     media_type: MediaType,
-    module_kind: deno_ast::ModuleKind,
+    module_kind: ModuleKind,
     source: &Arc<str>,
-  ) -> Result<String, AnyError> {
+  ) -> Result<String, EmitParsedSourceHelperError> {
     // Note: keep this in sync with the sync version below
     let helper = EmitParsedSourceHelper(self);
     match helper.pre_emit_parsed_source(specifier, module_kind, source) {
diff --git a/cli/main.rs b/cli/main.rs
index f97ea81e5d..a6b552c636 100644
--- a/cli/main.rs
+++ b/cli/main.rs
@@ -201,7 +201,7 @@ async fn run_subcommand(flags: Arc<Flags>) -> Result<i32, AnyError> {
         match result {
           Ok(v) => Ok(v),
           Err(script_err) => {
-            if let Some(ResolvePkgFolderFromDenoReqError::Byonm(ByonmResolvePkgFolderFromDenoReqError::UnmatchedReq(_))) = util::result::any_and_jserrorbox_downcast_ref::<ResolvePkgFolderFromDenoReqError>(&script_err) {
+            if let Some(worker::CreateCustomWorkerError::ResolvePkgFolderFromDenoReq(ResolvePkgFolderFromDenoReqError::Byonm(ByonmResolvePkgFolderFromDenoReqError::UnmatchedReq(_)))) = util::result::any_and_jserrorbox_downcast_ref::<worker::CreateCustomWorkerError>(&script_err) {
               if flags.node_modules_dir.is_none() {
                 let mut flags = flags.deref().clone();
                 let watch = match &flags.subcommand {
diff --git a/cli/module_loader.rs b/cli/module_loader.rs
index 2b0ebca986..7acb947491 100644
--- a/cli/module_loader.rs
+++ b/cli/module_loader.rs
@@ -13,8 +13,6 @@ use std::sync::Arc;
 
 use deno_ast::MediaType;
 use deno_ast::ModuleKind;
-use deno_core::anyhow::anyhow;
-use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
 use deno_core::error::ModuleLoaderError;
 use deno_core::futures::future::FutureExt;
@@ -45,6 +43,7 @@ use deno_lib::worker::ModuleLoaderFactory;
 use deno_resolver::npm::DenoInNpmPackageChecker;
 use deno_runtime::code_cache;
 use deno_runtime::deno_node::create_host_defined_options;
+use deno_runtime::deno_node::ops::require::UnableToGetCwdError;
 use deno_runtime::deno_node::NodeRequireLoader;
 use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_semver::npm::NpmPackageReqReference;
@@ -99,6 +98,11 @@ pub enum PrepareModuleLoadError {
   Check(#[from] CheckError),
   #[class(inherit)]
   #[error(transparent)]
+  AtomicWriteFileWithRetries(
+    #[from] crate::args::AtomicWriteFileWithRetriesError,
+  ),
+  #[class(inherit)]
+  #[error(transparent)]
   Other(#[from] JsErrorBox),
 }
 
@@ -419,6 +423,55 @@ impl ModuleLoaderFactory for CliModuleLoaderFactory {
   }
 }
 
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum LoadCodeSourceError {
+  #[class(inherit)]
+  #[error(transparent)]
+  NpmModuleLoad(crate::resolver::NpmModuleLoadError),
+  #[class(inherit)]
+  #[error(transparent)]
+  LoadPreparedModule(#[from] LoadPreparedModuleError),
+  #[class(generic)]
+  #[error("Loading unprepared module: {}{}", .specifier, .maybe_referrer.as_ref().map(|r| format!(", imported from: {}", r)).unwrap_or_default())]
+  LoadUnpreparedModule {
+    specifier: ModuleSpecifier,
+    maybe_referrer: Option<ModuleSpecifier>,
+  },
+}
+
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum LoadPreparedModuleError {
+  #[class(inherit)]
+  #[error(transparent)]
+  NpmModuleLoad(#[from] crate::emit::EmitParsedSourceHelperError),
+  #[class(inherit)]
+  #[error(transparent)]
+  LoadMaybeCjs(#[from] LoadMaybeCjsError),
+  #[class(inherit)]
+  #[error(transparent)]
+  Other(#[from] JsErrorBox),
+}
+
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum LoadMaybeCjsError {
+  #[class(inherit)]
+  #[error(transparent)]
+  NpmModuleLoad(#[from] crate::emit::EmitParsedSourceHelperError),
+  #[class(inherit)]
+  #[error(transparent)]
+  TranslateCjsToEsm(#[from] node_resolver::analyze::TranslateCjsToEsmError),
+}
+
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+#[class(inherit)]
+#[error("Could not resolve '{reference}'")]
+pub struct CouldNotResolveError {
+  reference: deno_semver::npm::NpmPackageNvReference,
+  #[source]
+  #[inherit]
+  source: node_resolver::errors::PackageSubpathResolveError,
+}
+
 struct CliModuleLoaderInner<TGraphContainer: ModuleGraphContainer> {
   lib: TsTypeLib,
   is_worker: bool,
@@ -443,7 +496,10 @@ impl<TGraphContainer: ModuleGraphContainer>
     maybe_referrer: Option<&ModuleSpecifier>,
     requested_module_type: RequestedModuleType,
   ) -> Result<ModuleSource, ModuleLoaderError> {
-    let code_source = self.load_code_source(specifier, maybe_referrer).await?;
+    let code_source = self
+      .load_code_source(specifier, maybe_referrer)
+      .await
+      .map_err(JsErrorBox::from_err)?;
     let code = if self.shared.is_inspecting
       || code_source.media_type == MediaType::Wasm
     {
@@ -504,7 +560,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     &self,
     specifier: &ModuleSpecifier,
     maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<ModuleCodeStringSource, AnyError> {
+  ) -> Result<ModuleCodeStringSource, LoadCodeSourceError> {
     if let Some(code_source) = self.load_prepared_module(specifier).await? {
       return Ok(code_source);
     }
@@ -513,14 +569,14 @@ impl<TGraphContainer: ModuleGraphContainer>
         .shared
         .npm_module_loader
         .load(specifier, maybe_referrer)
-        .await;
+        .await
+        .map_err(LoadCodeSourceError::NpmModuleLoad);
     }
 
-    let mut msg = format!("Loading unprepared module: {specifier}");
-    if let Some(referrer) = maybe_referrer {
-      msg = format!("{}, imported from: {}", msg, referrer.as_str());
-    }
-    Err(anyhow!(msg))
+    Err(LoadCodeSourceError::LoadUnpreparedModule {
+      specifier: specifier.clone(),
+      maybe_referrer: maybe_referrer.cloned(),
+    })
   }
 
   fn resolve_referrer(
@@ -543,7 +599,8 @@ impl<TGraphContainer: ModuleGraphContainer>
         .map_err(|e| e.into())
     } else {
       // this cwd check is slow, so try to avoid it
-      let cwd = std::env::current_dir().context("Unable to get CWD")?;
+      let cwd = std::env::current_dir()
+        .map_err(|e| JsErrorBox::from_err(UnableToGetCwdError(e)))?;
       deno_core::resolve_path(referrer, &cwd).map_err(|e| e.into())
     }
   }
@@ -622,8 +679,11 @@ impl<TGraphContainer: ModuleGraphContainer>
             ResolutionMode::Import,
             NodeResolutionKind::Execution,
           )
-          .with_context(|| {
-            format!("Could not resolve '{}'.", module.nv_reference)
+          .map_err(|source| {
+            JsErrorBox::from_err(CouldNotResolveError {
+              reference: module.nv_reference.clone(),
+              source,
+            })
           })?
       }
       Some(Module::Node(module)) => module.specifier.clone(),
@@ -644,7 +704,7 @@ impl<TGraphContainer: ModuleGraphContainer>
   async fn load_prepared_module(
     &self,
     specifier: &ModuleSpecifier,
-  ) -> Result<Option<ModuleCodeStringSource>, AnyError> {
+  ) -> Result<Option<ModuleCodeStringSource>, LoadPreparedModuleError> {
     // Note: keep this in sync with the sync version below
     let graph = self.graph_container.graph();
     match self.load_prepared_module_or_defer_emit(&graph, specifier)? {
@@ -676,7 +736,8 @@ impl<TGraphContainer: ModuleGraphContainer>
       }) => self
         .load_maybe_cjs(specifier, media_type, source)
         .await
-        .map(Some),
+        .map(Some)
+        .map_err(LoadPreparedModuleError::LoadMaybeCjs),
       None => Ok(None),
     }
   }
@@ -837,7 +898,7 @@ impl<TGraphContainer: ModuleGraphContainer>
     specifier: &ModuleSpecifier,
     media_type: MediaType,
     original_source: &Arc<str>,
-  ) -> Result<ModuleCodeStringSource, AnyError> {
+  ) -> Result<ModuleCodeStringSource, LoadMaybeCjsError> {
     let js_source = if media_type.is_emittable() {
       Cow::Owned(
         self
diff --git a/cli/node.rs b/cli/node.rs
index 892e25914a..f6411f5e53 100644
--- a/cli/node.rs
+++ b/cli/node.rs
@@ -5,13 +5,14 @@ use std::sync::Arc;
 
 use deno_ast::MediaType;
 use deno_ast::ModuleSpecifier;
-use deno_core::error::AnyError;
+use deno_error::JsErrorBox;
 use deno_graph::ParsedSourceStore;
 use deno_resolver::npm::DenoInNpmPackageChecker;
 use deno_runtime::deno_fs;
 use deno_runtime::deno_node::RealIsBuiltInNodeModuleChecker;
 use node_resolver::analyze::CjsAnalysis as ExtNodeCjsAnalysis;
 use node_resolver::analyze::CjsAnalysisExports;
+use node_resolver::analyze::CjsCodeAnalysisError;
 use node_resolver::analyze::CjsCodeAnalyzer;
 use node_resolver::analyze::NodeCodeTranslator;
 use serde::Deserialize;
@@ -75,7 +76,7 @@ impl CliCjsCodeAnalyzer {
     &self,
     specifier: &ModuleSpecifier,
     source: &str,
-  ) -> Result<CliCjsAnalysis, AnyError> {
+  ) -> Result<CliCjsAnalysis, CjsCodeAnalysisError> {
     let source_hash = CacheDBHash::from_hashable(source);
     if let Some(analysis) =
       self.cache.get_cjs_analysis(specifier.as_str(), source_hash)
@@ -102,9 +103,10 @@ impl CliCjsCodeAnalyzer {
       deno_core::unsync::spawn_blocking({
         let specifier = specifier.clone();
         let source: Arc<str> = source.into();
-        move || -> Result<_, AnyError> {
-          let parsed_source =
-            maybe_parsed_source.map(Ok).unwrap_or_else(|| {
+        move || -> Result<_, CjsCodeAnalysisError> {
+          let parsed_source = maybe_parsed_source
+            .map(Ok)
+            .unwrap_or_else(|| {
               deno_ast::parse_program(deno_ast::ParseParams {
                 specifier,
                 text: source,
@@ -113,7 +115,8 @@ impl CliCjsCodeAnalyzer {
                 scope_analysis: false,
                 maybe_syntax: None,
               })
-            })?;
+            })
+            .map_err(JsErrorBox::from_err)?;
           let is_script = parsed_source.compute_is_script();
           let is_cjs = cjs_tracker.is_cjs_with_known_is_script(
             parsed_source.specifier(),
@@ -151,7 +154,7 @@ impl CjsCodeAnalyzer for CliCjsCodeAnalyzer {
     &self,
     specifier: &ModuleSpecifier,
     source: Option<Cow<'a, str>>,
-  ) -> Result<ExtNodeCjsAnalysis<'a>, AnyError> {
+  ) -> Result<ExtNodeCjsAnalysis<'a>, CjsCodeAnalysisError> {
     let source = match source {
       Some(source) => source,
       None => {
diff --git a/cli/resolver.rs b/cli/resolver.rs
index 5677767fdd..b837ba51b1 100644
--- a/cli/resolver.rs
+++ b/cli/resolver.rs
@@ -1,6 +1,7 @@
 // Copyright 2018-2025 the Deno authors. MIT license.
 
 use std::borrow::Cow;
+use std::path::PathBuf;
 use std::sync::Arc;
 
 use async_trait::async_trait;
@@ -8,8 +9,6 @@ use dashmap::DashSet;
 use deno_ast::MediaType;
 use deno_config::workspace::MappedResolutionDiagnostic;
 use deno_config::workspace::MappedResolutionError;
-use deno_core::anyhow::Context;
-use deno_core::error::AnyError;
 use deno_core::url::Url;
 use deno_core::ModuleSourceCode;
 use deno_core::ModuleSpecifier;
@@ -84,6 +83,62 @@ pub struct NpmModuleLoader {
   node_code_translator: Arc<CliNodeCodeTranslator>,
 }
 
+#[derive(Debug, Error, deno_error::JsError)]
+pub enum NpmModuleLoadError {
+  #[class(inherit)]
+  #[error(transparent)]
+  NotSupportedKindInNpm(#[from] NotSupportedKindInNpmError),
+  #[class(inherit)]
+  #[error(transparent)]
+  ClosestPkgJson(#[from] node_resolver::errors::ClosestPkgJsonError),
+  #[class(inherit)]
+  #[error(transparent)]
+  TranslateCjsToEsm(#[from] node_resolver::analyze::TranslateCjsToEsmError),
+  #[class(inherit)]
+  #[error("{}", format_message(file_path, maybe_referrer))]
+  Fs {
+    file_path: PathBuf,
+    maybe_referrer: Option<ModuleSpecifier>,
+    #[source]
+    #[inherit]
+    source: deno_runtime::deno_io::fs::FsError,
+  },
+}
+
+fn format_message(
+  file_path: &std::path::Path,
+  maybe_referrer: &Option<ModuleSpecifier>,
+) -> String {
+  if file_path.is_dir() {
+    // directory imports are not allowed when importing from an
+    // ES module, so provide the user with a helpful error message
+    let dir_path = file_path;
+    let mut msg = "Directory import ".to_string();
+    msg.push_str(&dir_path.to_string_lossy());
+    if let Some(referrer) = maybe_referrer {
+      msg.push_str(" is not supported resolving import from ");
+      msg.push_str(referrer.as_str());
+      let entrypoint_name = ["index.mjs", "index.js", "index.cjs"]
+        .iter()
+        .find(|e| dir_path.join(e).is_file());
+      if let Some(entrypoint_name) = entrypoint_name {
+        msg.push_str("\nDid you mean to import ");
+        msg.push_str(entrypoint_name);
+        msg.push_str(" within the directory?");
+      }
+    }
+    msg
+  } else {
+    let mut msg = "Unable to load ".to_string();
+    msg.push_str(&file_path.to_string_lossy());
+    if let Some(referrer) = maybe_referrer {
+      msg.push_str(" imported from ");
+      msg.push_str(referrer.as_str());
+    }
+    msg
+  }
+}
+
 impl NpmModuleLoader {
   pub fn new(
     cjs_tracker: Arc<CliCjsTracker>,
@@ -101,50 +156,26 @@ impl NpmModuleLoader {
     &self,
     specifier: &ModuleSpecifier,
     maybe_referrer: Option<&ModuleSpecifier>,
-  ) -> Result<ModuleCodeStringSource, AnyError> {
+  ) -> Result<ModuleCodeStringSource, NpmModuleLoadError> {
     let file_path = specifier.to_file_path().unwrap();
     let code = self
       .fs
       .read_file_async(file_path.clone(), None)
       .await
-      .map_err(AnyError::from)
-      .with_context(|| {
-        if file_path.is_dir() {
-          // directory imports are not allowed when importing from an
-          // ES module, so provide the user with a helpful error message
-          let dir_path = file_path;
-          let mut msg = "Directory import ".to_string();
-          msg.push_str(&dir_path.to_string_lossy());
-          if let Some(referrer) = &maybe_referrer {
-            msg.push_str(" is not supported resolving import from ");
-            msg.push_str(referrer.as_str());
-            let entrypoint_name = ["index.mjs", "index.js", "index.cjs"]
-              .iter()
-              .find(|e| dir_path.join(e).is_file());
-            if let Some(entrypoint_name) = entrypoint_name {
-              msg.push_str("\nDid you mean to import ");
-              msg.push_str(entrypoint_name);
-              msg.push_str(" within the directory?");
-            }
-          }
-          msg
-        } else {
-          let mut msg = "Unable to load ".to_string();
-          msg.push_str(&file_path.to_string_lossy());
-          if let Some(referrer) = &maybe_referrer {
-            msg.push_str(" imported from ");
-            msg.push_str(referrer.as_str());
-          }
-          msg
-        }
+      .map_err(|source| NpmModuleLoadError::Fs {
+        file_path,
+        maybe_referrer: maybe_referrer.cloned(),
+        source,
       })?;
 
     let media_type = MediaType::from_specifier(specifier);
     if media_type.is_emittable() {
-      return Err(AnyError::from(NotSupportedKindInNpmError {
-        media_type,
-        specifier: specifier.clone(),
-      }));
+      return Err(NpmModuleLoadError::NotSupportedKindInNpm(
+        NotSupportedKindInNpmError {
+          media_type,
+          specifier: specifier.clone(),
+        },
+      ));
     }
 
     let code = if self.cjs_tracker.is_maybe_cjs(specifier, media_type)? {
diff --git a/cli/standalone/binary.rs b/cli/standalone/binary.rs
index 5334b4719d..54c82d17a3 100644
--- a/cli/standalone/binary.rs
+++ b/cli/standalone/binary.rs
@@ -37,6 +37,7 @@ use deno_core::futures::AsyncReadExt;
 use deno_core::futures::AsyncSeekExt;
 use deno_core::serde_json;
 use deno_core::url::Url;
+use deno_error::JsErrorBox;
 use deno_graph::ModuleGraph;
 use deno_lib::cache::DenoDir;
 use deno_lib::standalone::virtual_fs::FileSystemCaseSensitivity;
@@ -278,7 +279,7 @@ impl StandaloneModules {
   pub fn resolve_specifier<'a>(
     &'a self,
     specifier: &'a ModuleSpecifier,
-  ) -> Result<Option<&'a ModuleSpecifier>, AnyError> {
+  ) -> Result<Option<&'a ModuleSpecifier>, JsErrorBox> {
     if specifier.scheme() == "file" {
       Ok(Some(specifier))
     } else {
diff --git a/cli/standalone/mod.rs b/cli/standalone/mod.rs
index f2a0859e8f..1ab77a5a4c 100644
--- a/cli/standalone/mod.rs
+++ b/cli/standalone/mod.rs
@@ -414,7 +414,8 @@ impl ModuleLoader for EmbeddedModuleLoader {
           let code_source = shared
             .npm_module_loader
             .load(&original_specifier, maybe_referrer.as_ref())
-            .await?;
+            .await
+            .map_err(JsErrorBox::from_err)?;
           let code_cache_entry = shared.get_code_cache(
             &code_source.found_url,
             code_source.code.as_bytes(),
@@ -477,7 +478,8 @@ impl ModuleLoader for EmbeddedModuleLoader {
               let source = shared
                 .node_code_translator
                 .translate_cjs_to_esm(&module_specifier, Some(source))
-                .await?;
+                .await
+                .map_err(JsErrorBox::from_err)?;
               let module_source = match source {
                 Cow::Owned(source) => ModuleSourceCode::String(source.into()),
                 Cow::Borrowed(source) => {
diff --git a/cli/standalone/serialization.rs b/cli/standalone/serialization.rs
index ab345917a3..00a0a04997 100644
--- a/cli/standalone/serialization.rs
+++ b/cli/standalone/serialization.rs
@@ -17,6 +17,7 @@ use deno_core::url::Url;
 use deno_core::FastString;
 use deno_core::ModuleSourceCode;
 use deno_core::ModuleType;
+use deno_error::JsErrorBox;
 use deno_lib::standalone::virtual_fs::VirtualDirectoryEntries;
 use deno_npm::resolution::SerializedNpmResolutionSnapshot;
 use deno_npm::resolution::SerializedNpmResolutionSnapshotPackage;
@@ -441,12 +442,15 @@ impl RemoteModulesStore {
   pub fn resolve_specifier<'a>(
     &'a self,
     specifier: &'a Url,
-  ) -> Result<Option<&'a Url>, AnyError> {
+  ) -> Result<Option<&'a Url>, JsErrorBox> {
     let mut count = 0;
     let mut current = specifier;
     loop {
       if count > 10 {
-        bail!("Too many redirects resolving '{}'", specifier);
+        return Err(JsErrorBox::generic(format!(
+          "Too many redirects resolving '{}'",
+          specifier
+        )));
       }
       match self.specifiers.get(current) {
         Some(RemoteModulesStoreSpecifierValue::Redirect(to)) => {
diff --git a/cli/tools/bench/mod.rs b/cli/tools/bench/mod.rs
index 6a57c4ce6c..a316e60b52 100644
--- a/cli/tools/bench/mod.rs
+++ b/cli/tools/bench/mod.rs
@@ -48,6 +48,7 @@ use crate::util::fs::collect_specifiers;
 use crate::util::path::is_script_ext;
 use crate::util::path::matches_pattern_or_exact_path;
 use crate::worker::CliMainWorkerFactory;
+use crate::worker::CreateCustomWorkerError;
 
 mod mitata;
 mod reporters;
@@ -164,7 +165,7 @@ async fn bench_specifier(
   .await
   {
     Ok(()) => Ok(()),
-    Err(CoreError::Js(error)) => {
+    Err(CreateCustomWorkerError::Core(CoreError::Js(error))) => {
       sender.send(BenchEvent::UncaughtError(
         specifier.to_string(),
         Box::new(error),
@@ -182,7 +183,7 @@ async fn bench_specifier_inner(
   specifier: ModuleSpecifier,
   sender: &UnboundedSender<BenchEvent>,
   filter: TestFilter,
-) -> Result<(), CoreError> {
+) -> Result<(), CreateCustomWorkerError> {
   let mut worker = worker_factory
     .create_custom_worker(
       WorkerExecutionMode::Bench,
@@ -201,7 +202,7 @@ async fn bench_specifier_inner(
   // Ensure that there are no pending exceptions before we start running tests
   worker.run_up_to_duration(Duration::from_millis(0)).await?;
 
-  worker.dispatch_load_event()?;
+  worker.dispatch_load_event().map_err(CoreError::Js)?;
 
   let benchmarks = {
     let state_rc = worker.js_runtime.op_state();
@@ -236,11 +237,13 @@ async fn bench_specifier_inner(
       used_only,
       names: benchmarks.iter().map(|(d, _)| d.name.clone()).collect(),
     }))
-    .map_err(JsErrorBox::from_err)?;
+    .map_err(JsErrorBox::from_err)
+    .map_err(CoreError::JsBox)?;
   for (desc, function) in benchmarks {
     sender
       .send(BenchEvent::Wait(desc.id))
-      .map_err(JsErrorBox::from_err)?;
+      .map_err(JsErrorBox::from_err)
+      .map_err(CoreError::JsBox)?;
     let call = worker.js_runtime.call(&function);
     let result = worker
       .js_runtime
@@ -249,18 +252,26 @@ async fn bench_specifier_inner(
     let scope = &mut worker.js_runtime.handle_scope();
     let result = v8::Local::new(scope, result);
     let result = serde_v8::from_v8::<BenchResult>(scope, result)
-      .map_err(JsErrorBox::from_err)?;
+      .map_err(JsErrorBox::from_err)
+      .map_err(CoreError::JsBox)?;
     sender
       .send(BenchEvent::Result(desc.id, result))
-      .map_err(JsErrorBox::from_err)?;
+      .map_err(JsErrorBox::from_err)
+      .map_err(CoreError::JsBox)?;
   }
 
   // Ignore `defaultPrevented` of the `beforeunload` event. We don't allow the
   // event loop to continue beyond what's needed to await results.
-  worker.dispatch_beforeunload_event()?;
-  worker.dispatch_process_beforeexit_event()?;
-  worker.dispatch_unload_event()?;
-  worker.dispatch_process_exit_event()?;
+  worker
+    .dispatch_beforeunload_event()
+    .map_err(CoreError::Js)?;
+  worker
+    .dispatch_process_beforeexit_event()
+    .map_err(CoreError::Js)?;
+  worker.dispatch_unload_event().map_err(CoreError::Js)?;
+  worker
+    .dispatch_process_exit_event()
+    .map_err(CoreError::Js)?;
 
   // Ensure the worker has settled so we can catch any remaining unhandled rejections. We don't
   // want to wait forever here.
diff --git a/cli/tools/coverage/mod.rs b/cli/tools/coverage/mod.rs
index 9b6ef81ea3..53c08191f7 100644
--- a/cli/tools/coverage/mod.rs
+++ b/cli/tools/coverage/mod.rs
@@ -18,10 +18,12 @@ use deno_config::glob::PathOrPatternSet;
 use deno_core::anyhow::anyhow;
 use deno_core::anyhow::Context;
 use deno_core::error::AnyError;
+use deno_core::error::CoreError;
 use deno_core::serde_json;
 use deno_core::sourcemap::SourceMap;
 use deno_core::url::Url;
 use deno_core::LocalInspectorSession;
+use deno_error::JsErrorBox;
 use deno_resolver::npm::DenoInNpmPackageChecker;
 use node_resolver::InNpmPackageChecker;
 use regex::Regex;
@@ -53,7 +55,7 @@ pub struct CoverageCollector {
 
 #[async_trait::async_trait(?Send)]
 impl crate::worker::CoverageCollector for CoverageCollector {
-  async fn start_collecting(&mut self) -> Result<(), AnyError> {
+  async fn start_collecting(&mut self) -> Result<(), CoreError> {
     self.enable_debugger().await?;
     self.enable_profiler().await?;
     self
@@ -67,7 +69,7 @@ impl crate::worker::CoverageCollector for CoverageCollector {
     Ok(())
   }
 
-  async fn stop_collecting(&mut self) -> Result<(), AnyError> {
+  async fn stop_collecting(&mut self) -> Result<(), CoreError> {
     fs::create_dir_all(&self.dir)?;
 
     let script_coverages = self.take_precise_coverage().await?.result;
@@ -88,7 +90,8 @@ impl crate::worker::CoverageCollector for CoverageCollector {
       let filepath = self.dir.join(filename);
 
       let mut out = BufWriter::new(File::create(&filepath)?);
-      let coverage = serde_json::to_string(&script_coverage)?;
+      let coverage = serde_json::to_string(&script_coverage)
+        .map_err(JsErrorBox::from_err)?;
       let formatted_coverage =
         format_json(&filepath, &coverage, &Default::default())
           .ok()
@@ -111,7 +114,7 @@ impl CoverageCollector {
     Self { dir, session }
   }
 
-  async fn enable_debugger(&mut self) -> Result<(), AnyError> {
+  async fn enable_debugger(&mut self) -> Result<(), CoreError> {
     self
       .session
       .post_message::<()>("Debugger.enable", None)
@@ -119,7 +122,7 @@ impl CoverageCollector {
     Ok(())
   }
 
-  async fn enable_profiler(&mut self) -> Result<(), AnyError> {
+  async fn enable_profiler(&mut self) -> Result<(), CoreError> {
     self
       .session
       .post_message::<()>("Profiler.enable", None)
@@ -127,7 +130,7 @@ impl CoverageCollector {
     Ok(())
   }
 
-  async fn disable_debugger(&mut self) -> Result<(), AnyError> {
+  async fn disable_debugger(&mut self) -> Result<(), CoreError> {
     self
       .session
       .post_message::<()>("Debugger.disable", None)
@@ -135,7 +138,7 @@ impl CoverageCollector {
     Ok(())
   }
 
-  async fn disable_profiler(&mut self) -> Result<(), AnyError> {
+  async fn disable_profiler(&mut self) -> Result<(), CoreError> {
     self
       .session
       .post_message::<()>("Profiler.disable", None)
@@ -146,26 +149,28 @@ impl CoverageCollector {
   async fn start_precise_coverage(
     &mut self,
     parameters: cdp::StartPreciseCoverageArgs,
-  ) -> Result<cdp::StartPreciseCoverageResponse, AnyError> {
+  ) -> Result<cdp::StartPreciseCoverageResponse, CoreError> {
     let return_value = self
       .session
       .post_message("Profiler.startPreciseCoverage", Some(parameters))
       .await?;
 
-    let return_object = serde_json::from_value(return_value)?;
+    let return_object =
+      serde_json::from_value(return_value).map_err(JsErrorBox::from_err)?;
 
     Ok(return_object)
   }
 
   async fn take_precise_coverage(
     &mut self,
-  ) -> Result<cdp::TakePreciseCoverageResponse, AnyError> {
+  ) -> Result<cdp::TakePreciseCoverageResponse, CoreError> {
     let return_value = self
       .session
       .post_message::<()>("Profiler.takePreciseCoverage", None)
       .await?;
 
-    let return_object = serde_json::from_value(return_value)?;
+    let return_object =
+      serde_json::from_value(return_value).map_err(JsErrorBox::from_err)?;
 
     Ok(return_object)
   }
diff --git a/cli/tools/test/mod.rs b/cli/tools/test/mod.rs
index 21ee7e152d..cb49a9de95 100644
--- a/cli/tools/test/mod.rs
+++ b/cli/tools/test/mod.rs
@@ -87,6 +87,7 @@ use crate::util::path::is_script_ext;
 use crate::util::path::matches_pattern_or_exact_path;
 use crate::worker::CliMainWorkerFactory;
 use crate::worker::CoverageCollector;
+use crate::worker::CreateCustomWorkerError;
 
 mod channel;
 pub mod fmt;
@@ -614,7 +615,10 @@ async fn configure_main_worker(
   permissions_container: PermissionsContainer,
   worker_sender: TestEventWorkerSender,
   options: &TestSpecifierOptions,
-) -> Result<(Option<Box<dyn CoverageCollector>>, MainWorker), CoreError> {
+) -> Result<
+  (Option<Box<dyn CoverageCollector>>, MainWorker),
+  CreateCustomWorkerError,
+> {
   let mut worker = worker_factory
     .create_custom_worker(
       WorkerExecutionMode::Test,
@@ -647,7 +651,7 @@ async fn configure_main_worker(
         &worker.js_runtime.op_state(),
         TestEvent::UncaughtError(specifier.to_string(), Box::new(err)),
       )
-      .map_err(JsErrorBox::from_err)?;
+      .map_err(|e| CoreError::JsBox(JsErrorBox::from_err(e)))?;
       Ok(())
     }
     Err(err) => Err(err),
@@ -687,7 +691,7 @@ pub async fn test_specifier(
   .await
   {
     Ok(()) => Ok(()),
-    Err(CoreError::Js(err)) => {
+    Err(TestSpecifierError::Core(CoreError::Js(err))) => {
       send_test_event(
         &worker.js_runtime.op_state(),
         TestEvent::UncaughtError(specifier.to_string(), Box::new(err)),
@@ -698,6 +702,16 @@ pub async fn test_specifier(
   }
 }
 
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum TestSpecifierError {
+  #[class(inherit)]
+  #[error(transparent)]
+  Core(#[from] CoreError),
+  #[class(inherit)]
+  #[error(transparent)]
+  RunTestsForWorker(#[from] RunTestsForWorkerErr),
+}
+
 /// Test a single specifier as documentation containing test programs, an executable test module or
 /// both.
 #[allow(clippy::too_many_arguments)]
@@ -707,19 +721,21 @@ async fn test_specifier_inner(
   specifier: ModuleSpecifier,
   fail_fast_tracker: FailFastTracker,
   options: TestSpecifierOptions,
-) -> Result<(), CoreError> {
+) -> Result<(), TestSpecifierError> {
   // Ensure that there are no pending exceptions before we start running tests
   worker.run_up_to_duration(Duration::from_millis(0)).await?;
 
-  worker.dispatch_load_event()?;
+  worker.dispatch_load_event().map_err(CoreError::Js)?;
 
   run_tests_for_worker(worker, &specifier, &options, &fail_fast_tracker)
     .await?;
 
   // Ignore `defaultPrevented` of the `beforeunload` event. We don't allow the
   // event loop to continue beyond what's needed to await results.
-  worker.dispatch_beforeunload_event()?;
-  worker.dispatch_unload_event()?;
+  worker
+    .dispatch_beforeunload_event()
+    .map_err(CoreError::Js)?;
+  worker.dispatch_unload_event().map_err(CoreError::Js)?;
 
   // Ensure all output has been flushed
   _ = worker
@@ -780,12 +796,25 @@ pub fn send_test_event(
     .send(event)
 }
 
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum RunTestsForWorkerErr {
+  #[class(inherit)]
+  #[error(transparent)]
+  ChannelClosed(#[from] ChannelClosedError),
+  #[class(inherit)]
+  #[error(transparent)]
+  Core(#[from] CoreError),
+  #[class(inherit)]
+  #[error(transparent)]
+  SerdeV8(#[from] serde_v8::Error),
+}
+
 pub async fn run_tests_for_worker(
   worker: &mut MainWorker,
   specifier: &ModuleSpecifier,
   options: &TestSpecifierOptions,
   fail_fast_tracker: &FailFastTracker,
-) -> Result<(), AnyError> {
+) -> Result<(), RunTestsForWorkerErr> {
   let state_rc = worker.js_runtime.op_state();
   // Take whatever tests have been registered
   let TestContainer(tests, test_functions) =
@@ -814,7 +843,7 @@ async fn run_tests_for_worker_inner(
   test_functions: Vec<v8::Global<v8::Function>>,
   options: &TestSpecifierOptions,
   fail_fast_tracker: &FailFastTracker,
-) -> Result<(), AnyError> {
+) -> Result<(), RunTestsForWorkerErr> {
   let unfiltered = tests.len();
   let state_rc = worker.js_runtime.op_state();
 
@@ -1109,7 +1138,7 @@ async fn wait_for_activity_to_stabilize(
   before: RuntimeActivityStats,
   sanitize_ops: bool,
   sanitize_resources: bool,
-) -> Result<Option<RuntimeActivityDiff>, AnyError> {
+) -> Result<Option<RuntimeActivityDiff>, CoreError> {
   // First, check to see if there's any diff at all. If not, just continue.
   let after = stats.clone().capture(filter);
   let mut diff = RuntimeActivityStats::diff(&before, &after);
diff --git a/cli/util/result.rs b/cli/util/result.rs
index 0c1a75b1ce..e6d45be470 100644
--- a/cli/util/result.rs
+++ b/cli/util/result.rs
@@ -36,7 +36,7 @@ pub fn any_and_jserrorbox_downcast_ref<
     })
     .or_else(|| {
       err.downcast_ref::<CoreError>().and_then(|e| match e {
-        CoreError::JsNative(e) => e.as_any().downcast_ref::<E>(),
+        CoreError::JsBox(e) => e.as_any().downcast_ref::<E>(),
         _ => None,
       })
     })
diff --git a/cli/worker.rs b/cli/worker.rs
index cf301de83e..3a11f56c71 100644
--- a/cli/worker.rs
+++ b/cli/worker.rs
@@ -4,8 +4,6 @@ use std::path::Path;
 use std::sync::Arc;
 
 use deno_ast::ModuleSpecifier;
-use deno_core::anyhow::bail;
-use deno_core::error::AnyError;
 use deno_core::error::CoreError;
 use deno_core::futures::FutureExt;
 use deno_core::v8;
@@ -19,6 +17,7 @@ use deno_runtime::deno_permissions::PermissionsContainer;
 use deno_runtime::worker::MainWorker;
 use deno_runtime::WorkerExecutionMode;
 use deno_semver::npm::NpmPackageReqReference;
+use node_resolver::errors::ResolvePkgJsonBinExportError;
 use node_resolver::NodeResolutionKind;
 use node_resolver::ResolutionMode;
 use sys_traits::EnvCurrentDir;
@@ -52,8 +51,8 @@ pub trait CliCodeCache: code_cache::CodeCache {
 
 #[async_trait::async_trait(?Send)]
 pub trait CoverageCollector: Send + Sync {
-  async fn start_collecting(&mut self) -> Result<(), AnyError>;
-  async fn stop_collecting(&mut self) -> Result<(), AnyError>;
+  async fn start_collecting(&mut self) -> Result<(), CoreError>;
+  async fn stop_collecting(&mut self) -> Result<(), CoreError>;
 }
 
 pub type CreateHmrRunnerCb = Box<
@@ -91,7 +90,7 @@ impl CliMainWorker {
     self.worker.into_main_worker()
   }
 
-  pub async fn setup_repl(&mut self) -> Result<(), AnyError> {
+  pub async fn setup_repl(&mut self) -> Result<(), CoreError> {
     self.worker.run_event_loop(false).await?;
     Ok(())
   }
@@ -172,7 +171,7 @@ impl CliMainWorker {
     Ok(self.worker.exit_code())
   }
 
-  pub async fn run_for_watcher(self) -> Result<(), AnyError> {
+  pub async fn run_for_watcher(self) -> Result<(), CoreError> {
     /// The FileWatcherModuleExecutor provides module execution with safe dispatching of life-cycle events by tracking the
     /// state of any pending events and emitting accordingly on drop in the case of a future
     /// cancellation.
@@ -191,7 +190,7 @@ impl CliMainWorker {
 
       /// Execute the given main module emitting load and unload events before and after execution
       /// respectively.
-      pub async fn execute(&mut self) -> Result<(), AnyError> {
+      pub async fn execute(&mut self) -> Result<(), CoreError> {
         self.inner.execute_main_module().await?;
         self.inner.worker.dispatch_load_event()?;
         self.pending_unload = true;
@@ -245,7 +244,7 @@ impl CliMainWorker {
 
   pub async fn maybe_setup_hmr_runner(
     &mut self,
-  ) -> Result<Option<Box<dyn HmrRunner>>, AnyError> {
+  ) -> Result<Option<Box<dyn HmrRunner>>, CoreError> {
     let Some(setup_hmr_runner) = self.shared.create_hmr_runner.as_ref() else {
       return Ok(None);
     };
@@ -267,7 +266,7 @@ impl CliMainWorker {
 
   pub async fn maybe_setup_coverage_collector(
     &mut self,
-  ) -> Result<Option<Box<dyn CoverageCollector>>, AnyError> {
+  ) -> Result<Option<Box<dyn CoverageCollector>>, CoreError> {
     let Some(create_coverage_collector) =
       self.shared.create_coverage_collector.as_ref()
     else {
@@ -296,6 +295,58 @@ impl CliMainWorker {
   }
 }
 
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum ResolveBinaryEntrypointError {
+  #[class(inherit)]
+  #[error(transparent)]
+  ResolvePkgJsonBinExport(ResolvePkgJsonBinExportError),
+  #[class(generic)]
+  #[error("{original:#}\n\nFallback failed: {fallback:#}")]
+  Fallback {
+    fallback: ResolveBinaryEntrypointFallbackError,
+    original: ResolvePkgJsonBinExportError,
+  },
+}
+
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum ResolveBinaryEntrypointFallbackError {
+  #[class(inherit)]
+  #[error(transparent)]
+  PackageSubpathResolve(node_resolver::errors::PackageSubpathResolveError),
+  #[class(generic)]
+  #[error("Cannot find module '{0}'")]
+  ModuleNotFound(ModuleSpecifier),
+}
+
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum CreateCustomWorkerError {
+  #[class(inherit)]
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[class(inherit)]
+  #[error(transparent)]
+  Core(#[from] CoreError),
+  #[class(inherit)]
+  #[error(transparent)]
+  ResolvePkgFolderFromDenoReq(
+    #[from] deno_resolver::npm::ResolvePkgFolderFromDenoReqError,
+  ),
+  #[class(inherit)]
+  #[error(transparent)]
+  UrlParse(#[from] deno_core::url::ParseError),
+  #[class(inherit)]
+  #[error(transparent)]
+  ResolveBinaryEntrypoint(#[from] ResolveBinaryEntrypointError),
+  #[class(inherit)]
+  #[error(transparent)]
+  NpmPackageReq(JsErrorBox),
+  #[class(inherit)]
+  #[error(transparent)]
+  AtomicWriteFileWithRetries(
+    #[from] crate::args::AtomicWriteFileWithRetriesError,
+  ),
+}
+
 pub struct CliMainWorkerFactory {
   lib_main_worker_factory: LibMainWorkerFactory<CliSys>,
   maybe_lockfile: Option<Arc<CliLockfile>>,
@@ -344,7 +395,7 @@ impl CliMainWorkerFactory {
     &self,
     mode: WorkerExecutionMode,
     main_module: ModuleSpecifier,
-  ) -> Result<CliMainWorker, CoreError> {
+  ) -> Result<CliMainWorker, CreateCustomWorkerError> {
     self
       .create_custom_worker(
         mode,
@@ -363,7 +414,7 @@ impl CliMainWorkerFactory {
     permissions: PermissionsContainer,
     custom_extensions: Vec<Extension>,
     stdio: deno_runtime::deno_io::Stdio,
-  ) -> Result<CliMainWorker, CoreError> {
+  ) -> Result<CliMainWorker, CreateCustomWorkerError> {
     let main_module = if let Ok(package_ref) =
       NpmPackageReqReference::from_specifier(&main_module)
     {
@@ -381,19 +432,20 @@ impl CliMainWorkerFactory {
               PackageCaching::All
             },
           )
-          .await?;
+          .await
+          .map_err(CreateCustomWorkerError::NpmPackageReq)?;
       }
 
       // use a fake referrer that can be used to discover the package.json if necessary
-      let referrer = ModuleSpecifier::from_directory_path(
-        self.sys.env_current_dir().map_err(JsErrorBox::from_err)?,
-      )
-      .unwrap()
-      .join("package.json")?;
-      let package_folder = self
-        .npm_resolver
-        .resolve_pkg_folder_from_deno_module_req(package_ref.req(), &referrer)
-        .map_err(JsErrorBox::from_err)?;
+      let referrer =
+        ModuleSpecifier::from_directory_path(self.sys.env_current_dir()?)
+          .unwrap()
+          .join("package.json")?;
+      let package_folder =
+        self.npm_resolver.resolve_pkg_folder_from_deno_module_req(
+          package_ref.req(),
+          &referrer,
+        )?;
       let main_module = self
         .resolve_binary_entrypoint(&package_folder, package_ref.sub_path())?;
 
@@ -447,7 +499,7 @@ impl CliMainWorkerFactory {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<ModuleSpecifier, AnyError> {
+  ) -> Result<ModuleSpecifier, ResolveBinaryEntrypointError> {
     match self
       .node_resolver
       .resolve_binary_export(package_folder, sub_path)
@@ -459,10 +511,13 @@ impl CliMainWorkerFactory {
           self.resolve_binary_entrypoint_fallback(package_folder, sub_path);
         match result {
           Ok(Some(specifier)) => Ok(specifier),
-          Ok(None) => Err(original_err.into()),
-          Err(fallback_err) => {
-            bail!("{:#}\n\nFallback failed: {:#}", original_err, fallback_err)
-          }
+          Ok(None) => Err(
+            ResolveBinaryEntrypointError::ResolvePkgJsonBinExport(original_err),
+          ),
+          Err(fallback_err) => Err(ResolveBinaryEntrypointError::Fallback {
+            original: original_err,
+            fallback: fallback_err,
+          }),
         }
       }
     }
@@ -473,7 +528,7 @@ impl CliMainWorkerFactory {
     &self,
     package_folder: &Path,
     sub_path: Option<&str>,
-  ) -> Result<Option<ModuleSpecifier>, AnyError> {
+  ) -> Result<Option<ModuleSpecifier>, ResolveBinaryEntrypointFallbackError> {
     // only fallback if the user specified a sub path
     if sub_path.is_none() {
       // it's confusing to users if the package doesn't have any binary
@@ -490,7 +545,8 @@ impl CliMainWorkerFactory {
         /* referrer */ None,
         ResolutionMode::Import,
         NodeResolutionKind::Execution,
-      )?;
+      )
+      .map_err(ResolveBinaryEntrypointFallbackError::PackageSubpathResolve)?;
     if specifier
       .to_file_path()
       .map(|p| p.exists())
@@ -498,7 +554,9 @@ impl CliMainWorkerFactory {
     {
       Ok(Some(specifier))
     } else {
-      bail!("Cannot find module '{}'", specifier)
+      Err(ResolveBinaryEntrypointFallbackError::ModuleNotFound(
+        specifier,
+      ))
     }
   }
 }
diff --git a/ext/net/quic.rs b/ext/net/quic.rs
index e075745495..af13a3f009 100644
--- a/ext/net/quic.rs
+++ b/ext/net/quic.rs
@@ -99,9 +99,6 @@ pub enum QuicError {
   #[class(range)]
   #[error("Connection has reached the maximum number of concurrent outgoing {0} streams")]
   MaxStreams(&'static str),
-  #[class(generic)]
-  #[error("{0}")]
-  Core(#[from] deno_core::error::AnyError),
   #[class(inherit)]
   #[error(transparent)]
   Other(#[from] JsErrorBox),
diff --git a/ext/node/ops/require.rs b/ext/node/ops/require.rs
index bff0cd79ed..c0e54993ae 100644
--- a/ext/node/ops/require.rs
+++ b/ext/node/ops/require.rs
@@ -106,10 +106,15 @@ pub enum RequireErrorKind {
     JsErrorBox,
   ),
   #[class(inherit)]
-  #[error("Unable to get CWD: {0}")]
-  UnableToGetCwd(#[inherit] std::io::Error),
+  #[error(transparent)]
+  UnableToGetCwd(UnableToGetCwdError),
 }
 
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+#[error("Unable to get CWD")]
+#[class(inherit)]
+pub struct UnableToGetCwdError(#[source] pub std::io::Error);
+
 #[op2]
 #[serde]
 pub fn op_require_init_paths() -> Vec<String> {
@@ -177,7 +182,7 @@ pub fn op_require_node_module_paths<
   } else {
     let current_dir = &sys
       .env_current_dir()
-      .map_err(RequireErrorKind::UnableToGetCwd)?;
+      .map_err(|e| RequireErrorKind::UnableToGetCwd(UnableToGetCwdError(e)))?;
     normalize_path(current_dir.join(from))
   };
 
diff --git a/resolvers/node/analyze.rs b/resolvers/node/analyze.rs
index e144e2b8fb..a67023d1e1 100644
--- a/resolvers/node/analyze.rs
+++ b/resolvers/node/analyze.rs
@@ -6,8 +6,7 @@ use std::collections::HashSet;
 use std::path::Path;
 use std::path::PathBuf;
 
-use anyhow::Context;
-use anyhow::Error as AnyError;
+use deno_error::JsErrorBox;
 use deno_path_util::url_from_file_path;
 use deno_path_util::url_to_file_path;
 use futures::future::LocalBoxFuture;
@@ -43,6 +42,16 @@ pub struct CjsAnalysisExports {
   pub reexports: Vec<String>,
 }
 
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum CjsCodeAnalysisError {
+  #[class(inherit)]
+  #[error(transparent)]
+  ClosestPkgJson(#[from] crate::errors::ClosestPkgJsonError),
+  #[class(inherit)]
+  #[error(transparent)]
+  Other(#[from] JsErrorBox),
+}
+
 /// Code analyzer for CJS and ESM files.
 #[async_trait::async_trait(?Send)]
 pub trait CjsCodeAnalyzer {
@@ -57,7 +66,28 @@ pub trait CjsCodeAnalyzer {
     &self,
     specifier: &Url,
     maybe_source: Option<Cow<'a, str>>,
-  ) -> Result<CjsAnalysis<'a>, AnyError>;
+  ) -> Result<CjsAnalysis<'a>, CjsCodeAnalysisError>;
+}
+
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum TranslateCjsToEsmError {
+  #[class(inherit)]
+  #[error(transparent)]
+  CjsCodeAnalysis(#[from] CjsCodeAnalysisError),
+  #[class(inherit)]
+  #[error(transparent)]
+  ExportAnalysis(#[from] JsErrorBox),
+}
+
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+#[class(generic)]
+#[error("Could not load '{reexport}' ({reexport_specifier}) referenced from {referrer}")]
+pub struct CjsAnalysisCouldNotLoadError {
+  reexport: String,
+  reexport_specifier: Url,
+  referrer: Url,
+  #[source]
+  source: CjsCodeAnalysisError,
 }
 
 pub struct NodeCodeTranslator<
@@ -128,7 +158,7 @@ impl<
     &self,
     entry_specifier: &Url,
     source: Option<Cow<'a, str>>,
-  ) -> Result<Cow<'a, str>, AnyError> {
+  ) -> Result<Cow<'a, str>, TranslateCjsToEsmError> {
     let mut temp_var_count = 0;
 
     let analysis = self
@@ -164,7 +194,7 @@ impl<
       // surface errors afterwards in a deterministic way
       if !errors.is_empty() {
         errors.sort_by_cached_key(|e| e.to_string());
-        return Err(errors.remove(0));
+        return Err(TranslateCjsToEsmError::ExportAnalysis(errors.remove(0)));
       }
     }
 
@@ -208,7 +238,7 @@ impl<
     all_exports: &mut BTreeSet<String>,
     // this goes through the modules concurrently, so collect
     // the errors in order to be deterministic
-    errors: &mut Vec<anyhow::Error>,
+    errors: &mut Vec<JsErrorBox>,
   ) {
     struct Analysis {
       reexport_specifier: url::Url,
@@ -216,7 +246,7 @@ impl<
       analysis: CjsAnalysis<'static>,
     }
 
-    type AnalysisFuture<'a> = LocalBoxFuture<'a, Result<Analysis, AnyError>>;
+    type AnalysisFuture<'a> = LocalBoxFuture<'a, Result<Analysis, JsErrorBox>>;
 
     let mut handled_reexports: HashSet<Url> = HashSet::default();
     handled_reexports.insert(entry_specifier.clone());
@@ -227,7 +257,7 @@ impl<
       |referrer: url::Url,
        reexports: Vec<String>,
        analyze_futures: &mut FuturesUnordered<AnalysisFuture<'a>>,
-       errors: &mut Vec<anyhow::Error>| {
+       errors: &mut Vec<JsErrorBox>| {
         // 1. Resolve the re-exports and start a future to analyze each one
         for reexport in reexports {
           let result = self.resolve(
@@ -256,11 +286,13 @@ impl<
             let analysis = cjs_code_analyzer
               .analyze_cjs(&reexport_specifier, None)
               .await
-              .with_context(|| {
-                format!(
-                  "Could not load '{}' ({}) referenced from {}",
-                  reexport, reexport_specifier, referrer
-                )
+              .map_err(|source| {
+                JsErrorBox::from_err(CjsAnalysisCouldNotLoadError {
+                  reexport,
+                  reexport_specifier: reexport_specifier.clone(),
+                  referrer: referrer.clone(),
+                  source,
+                })
               })?;
 
             Ok(Analysis {
@@ -297,11 +329,10 @@ impl<
       match analysis {
         CjsAnalysis::Esm(_) => {
           // todo(dsherret): support this once supporting requiring ES modules
-          errors.push(anyhow::anyhow!(
+          errors.push(JsErrorBox::generic(format!(
             "Cannot require ES module '{}' from '{}'",
-            reexport_specifier,
-            referrer,
-          ));
+            reexport_specifier, referrer,
+          )));
         }
         CjsAnalysis::Cjs(analysis) => {
           if !analysis.reexports.is_empty() {
@@ -331,7 +362,7 @@ impl<
     referrer: &Url,
     conditions: &[&str],
     resolution_kind: NodeResolutionKind,
-  ) -> Result<Option<Url>, AnyError> {
+  ) -> Result<Option<Url>, JsErrorBox> {
     if specifier.starts_with('/') {
       todo!();
     }
@@ -341,7 +372,7 @@ impl<
       if let Some(parent) = referrer_path.parent() {
         return self
           .file_extension_probe(parent.join(specifier), &referrer_path)
-          .and_then(|p| url_from_file_path(&p).map_err(AnyError::from))
+          .and_then(|p| url_from_file_path(&p).map_err(JsErrorBox::from_err))
           .map(Some);
       } else {
         todo!();
@@ -364,13 +395,14 @@ impl<
       {
         return Ok(None);
       }
-      other => other,
-    }?;
+      other => other.map_err(JsErrorBox::from_err)?,
+    };
 
     let package_json_path = module_dir.join("package.json");
     let maybe_package_json = self
       .pkg_json_resolver
-      .load_package_json(&package_json_path)?;
+      .load_package_json(&package_json_path)
+      .map_err(JsErrorBox::from_err)?;
     if let Some(package_json) = maybe_package_json {
       if let Some(exports) = &package_json.exports {
         return Some(
@@ -385,7 +417,7 @@ impl<
               conditions,
               resolution_kind,
             )
-            .map_err(AnyError::from),
+            .map_err(JsErrorBox::from_err),
         )
         .transpose();
       }
@@ -398,29 +430,40 @@ impl<
           let package_json_path = d.join("package.json");
           let maybe_package_json = self
             .pkg_json_resolver
-            .load_package_json(&package_json_path)?;
+            .load_package_json(&package_json_path)
+            .map_err(JsErrorBox::from_err)?;
           if let Some(package_json) = maybe_package_json {
             if let Some(main) =
               package_json.main(deno_package_json::NodeModuleKind::Cjs)
             {
-              return Ok(Some(url_from_file_path(&d.join(main).clean())?));
+              return Ok(Some(
+                url_from_file_path(&d.join(main).clean())
+                  .map_err(JsErrorBox::from_err)?,
+              ));
             }
           }
 
-          return Ok(Some(url_from_file_path(&d.join("index.js").clean())?));
+          return Ok(Some(
+            url_from_file_path(&d.join("index.js").clean())
+              .map_err(JsErrorBox::from_err)?,
+          ));
         }
         return self
           .file_extension_probe(d, &referrer_path)
-          .and_then(|p| url_from_file_path(&p).map_err(AnyError::from))
+          .and_then(|p| url_from_file_path(&p).map_err(JsErrorBox::from_err))
           .map(Some);
       } else if let Some(main) =
         package_json.main(deno_package_json::NodeModuleKind::Cjs)
       {
-        return Ok(Some(url_from_file_path(&module_dir.join(main).clean())?));
+        return Ok(Some(
+          url_from_file_path(&module_dir.join(main).clean())
+            .map_err(JsErrorBox::from_err)?,
+        ));
       } else {
-        return Ok(Some(url_from_file_path(
-          &module_dir.join("index.js").clean(),
-        )?));
+        return Ok(Some(
+          url_from_file_path(&module_dir.join("index.js").clean())
+            .map_err(JsErrorBox::from_err)?,
+        ));
       }
     }
 
@@ -436,7 +479,9 @@ impl<
         parent.join("node_modules").join(specifier)
       };
       if let Ok(path) = self.file_extension_probe(path, &referrer_path) {
-        return Ok(Some(url_from_file_path(&path)?));
+        return Ok(Some(
+          url_from_file_path(&path).map_err(JsErrorBox::from_err)?,
+        ));
       }
       last = parent;
     }
@@ -448,7 +493,7 @@ impl<
     &self,
     p: PathBuf,
     referrer: &Path,
-  ) -> Result<PathBuf, AnyError> {
+  ) -> Result<PathBuf, JsErrorBox> {
     let p = p.clean();
     if self.sys.fs_exists_no_err(&p) {
       let file_name = p.file_name().unwrap();
@@ -638,13 +683,13 @@ fn parse_specifier(specifier: &str) -> Option<(String, String)> {
   Some((package_name, package_subpath))
 }
 
-fn not_found(path: &str, referrer: &Path) -> AnyError {
+fn not_found(path: &str, referrer: &Path) -> JsErrorBox {
   let msg = format!(
     "[ERR_MODULE_NOT_FOUND] Cannot find module \"{}\" imported from \"{}\"",
     path,
     referrer.to_string_lossy()
   );
-  std::io::Error::new(std::io::ErrorKind::NotFound, msg).into()
+  JsErrorBox::from_err(std::io::Error::new(std::io::ErrorKind::NotFound, msg))
 }
 
 fn to_double_quote_string(text: &str) -> String {
diff --git a/runtime/fs_util.rs b/runtime/fs_util.rs
index 7788a97170..5dca3a55ee 100644
--- a/runtime/fs_util.rs
+++ b/runtime/fs_util.rs
@@ -4,11 +4,12 @@ use std::path::Path;
 use std::path::PathBuf;
 
 use deno_core::anyhow::Context;
-use deno_core::error::AnyError;
 use deno_path_util::normalize_path;
 
 #[inline]
-pub fn resolve_from_cwd(path: &Path) -> Result<PathBuf, AnyError> {
+pub fn resolve_from_cwd(
+  path: &Path,
+) -> Result<PathBuf, deno_core::anyhow::Error> {
   if path.is_absolute() {
     Ok(normalize_path(path))
   } else {
diff --git a/runtime/inspector_server.rs b/runtime/inspector_server.rs
index 75e9668db4..cf043c97ac 100644
--- a/runtime/inspector_server.rs
+++ b/runtime/inspector_server.rs
@@ -10,8 +10,6 @@ use std::process;
 use std::rc::Rc;
 use std::thread;
 
-use deno_core::anyhow::Context;
-use deno_core::error::AnyError;
 use deno_core::futures::channel::mpsc;
 use deno_core::futures::channel::mpsc::UnboundedReceiver;
 use deno_core::futures::channel::mpsc::UnboundedSender;
@@ -49,17 +47,33 @@ pub struct InspectorServer {
   thread_handle: Option<thread::JoinHandle<()>>,
 }
 
+#[derive(Debug, thiserror::Error, deno_error::JsError)]
+pub enum InspectorServerError {
+  #[class(inherit)]
+  #[error(transparent)]
+  Io(#[from] std::io::Error),
+  #[class(inherit)]
+  #[error("Failed to start inspector server at \"{host}\"")]
+  Connect {
+    host: SocketAddr,
+    #[source]
+    #[inherit]
+    source: std::io::Error,
+  },
+}
+
 impl InspectorServer {
-  pub fn new(host: SocketAddr, name: &'static str) -> Result<Self, AnyError> {
+  pub fn new(
+    host: SocketAddr,
+    name: &'static str,
+  ) -> Result<Self, InspectorServerError> {
     let (register_inspector_tx, register_inspector_rx) =
       mpsc::unbounded::<InspectorInfo>();
 
     let (shutdown_server_tx, shutdown_server_rx) = broadcast::channel(1);
 
-    let tcp_listener =
-      std::net::TcpListener::bind(host).with_context(|| {
-        format!("Failed to start inspector server at \"{}\"", host)
-      })?;
+    let tcp_listener = std::net::TcpListener::bind(host)
+      .map_err(|source| InspectorServerError::Connect { host, source })?;
     tcp_listener.set_nonblocking(true)?;
 
     let thread_handle = thread::spawn(move || {