diff --git a/cli/src/cli_util.rs b/cli/src/cli_util.rs
index 89d3119afe..d1d8a523f8 100644
--- a/cli/src/cli_util.rs
+++ b/cli/src/cli_util.rs
@@ -57,9 +57,9 @@ use jj_lib::backend::CommitId;
 use jj_lib::backend::MergedTreeId;
 use jj_lib::backend::TreeValue;
 use jj_lib::commit::Commit;
-use jj_lib::config::ConfigError;
+use jj_lib::config::ConfigGetError;
+use jj_lib::config::ConfigGetResultExt as _;
 use jj_lib::config::ConfigNamePathBuf;
-use jj_lib::config::ConfigResultExt as _;
 use jj_lib::config::StackedConfig;
 use jj_lib::conflicts::ConflictMarkerStyle;
 use jj_lib::file_util;
@@ -2691,8 +2691,16 @@ fn load_template_aliases(
         let table = match layer.look_up_table(&table_name) {
             Ok(Some(table)) => table,
             Ok(None) => continue,
-            // TODO: rewrite error construction after migrating to toml_edit
-            Err(item) => return Err(item.clone().into_table().unwrap_err().into()),
+            Err(item) => {
+                // TODO: rewrite error construction after migrating to toml_edit
+                let error = item.clone().into_table().unwrap_err();
+                return Err(ConfigGetError::Type {
+                    name: table_name.to_string(),
+                    error: error.into(),
+                    source_path: layer.path.clone(),
+                }
+                .into());
+            }
         };
         // TODO: remove sorting after migrating to toml_edit
         for (decl, value) in table.iter().sorted_by_key(|&(decl, _)| decl) {
@@ -2721,7 +2729,7 @@ pub struct LogContentFormat {
 
 impl LogContentFormat {
     /// Creates new formatting helper for the terminal.
-    pub fn new(ui: &Ui, settings: &UserSettings) -> Result<Self, ConfigError> {
+    pub fn new(ui: &Ui, settings: &UserSettings) -> Result<Self, ConfigGetError> {
         Ok(LogContentFormat {
             width: ui.term_width(),
             word_wrap: settings.get_bool("ui.log-word-wrap")?,
@@ -2763,9 +2771,7 @@ pub fn run_ui_editor(settings: &UserSettings, edit_path: &Path) -> Result<(), Co
     // Work around UNC paths not being well supported on Windows (no-op for
     // non-Windows): https://github.com/martinvonz/jj/issues/3986
     let edit_path = dunce::simplified(edit_path);
-    let editor: CommandNameAndArgs = settings
-        .get("ui.editor")
-        .map_err(|err| config_error_with_message("Invalid `ui.editor`", err))?;
+    let editor: CommandNameAndArgs = settings.get("ui.editor")?;
     let mut cmd = editor.to_command();
     cmd.arg(edit_path);
     tracing::info!(?cmd, "running editor");
@@ -3084,7 +3090,7 @@ impl ValueParserFactory for RevisionArg {
 fn get_string_or_array(
     config: &StackedConfig,
     key: &'static str,
-) -> Result<Vec<String>, ConfigError> {
+) -> Result<Vec<String>, ConfigGetError> {
     config
         .get(key)
         .map(|string| vec![string])
@@ -3539,16 +3545,7 @@ impl CliRunner {
             config_env.reset_repo_path(loader.repo_path());
             config_env.reload_repo_config(&mut config)?;
         }
-        ui.reset(&config).map_err(|e| {
-            let user_config_path = config_env.existing_user_config_path();
-            let repo_config_path = config_env.existing_repo_config_path();
-            let paths = [repo_config_path, user_config_path]
-                .into_iter()
-                .flatten()
-                .map(|path| format!("- {}", path.display()))
-                .join("\n");
-            e.hinted(format!("Check the following config files:\n{paths}"))
-        })?;
+        ui.reset(&config)?;
 
         if env::var_os("COMPLETE").is_some() {
             return handle_shell_completion(ui, &self.app, &config, &cwd);
diff --git a/cli/src/command_error.rs b/cli/src/command_error.rs
index 67ec8d9e96..d98d9acf9b 100644
--- a/cli/src/command_error.rs
+++ b/cli/src/command_error.rs
@@ -23,6 +23,7 @@ use std::sync::Arc;
 use itertools::Itertools as _;
 use jj_lib::backend::BackendError;
 use jj_lib::config::ConfigError;
+use jj_lib::config::ConfigGetError;
 use jj_lib::dsl_util::Diagnostics;
 use jj_lib::fileset::FilePatternParseError;
 use jj_lib::fileset::FilesetParseError;
@@ -251,6 +252,20 @@ impl From<ConfigEnvError> for CommandError {
     }
 }
 
+impl From<ConfigGetError> for CommandError {
+    fn from(err: ConfigGetError) -> Self {
+        let hint = match &err {
+            ConfigGetError::NotFound { .. } => None,
+            ConfigGetError::Type { source_path, .. } => source_path
+                .as_ref()
+                .map(|path| format!("Check the config file: {}", path.display())),
+        };
+        let mut cmd_err = config_error(err);
+        cmd_err.extend_hints(hint);
+        cmd_err
+    }
+}
+
 impl From<RewriteRootCommit> for CommandError {
     fn from(err: RewriteRootCommit) -> Self {
         internal_error_with_message("Attempted to rewrite the root commit", err)
diff --git a/cli/src/commands/config/get.rs b/cli/src/commands/config/get.rs
index 3ebf579e42..8db273f202 100644
--- a/cli/src/commands/config/get.rs
+++ b/cli/src/commands/config/get.rs
@@ -13,14 +13,15 @@
 // limitations under the License.
 
 use std::io::Write as _;
+use std::path::PathBuf;
 
 use clap_complete::ArgValueCandidates;
 use jj_lib::config::ConfigError;
+use jj_lib::config::ConfigGetError;
 use jj_lib::config::ConfigNamePathBuf;
 use tracing::instrument;
 
 use crate::cli_util::CommandHelper;
-use crate::command_error::config_error;
 use crate::command_error::CommandError;
 use crate::complete;
 use crate::ui::Ui;
@@ -48,29 +49,19 @@ pub fn cmd_config_get(
     args: &ConfigGetArgs,
 ) -> Result<(), CommandError> {
     let value = command.settings().get_value(&args.name)?;
-    let stringified = value.into_string().map_err(|err| match err {
-        ConfigError::Type {
-            origin,
-            unexpected,
-            expected,
-            key,
-        } => {
-            let expected = format!("a value convertible to {expected}");
-            // Copied from `impl fmt::Display for ConfigError`. We can't use
-            // the `Display` impl directly because `expected` is required to
-            // be a `'static str`.
-            let mut buf = String::new();
-            use std::fmt::Write;
-            write!(buf, "invalid type: {unexpected}, expected {expected}").unwrap();
-            if let Some(key) = key {
-                write!(buf, " for key `{key}`").unwrap();
+    let stringified = value.into_string().map_err(|err| -> CommandError {
+        match err {
+            ConfigError::Type {
+                origin, unexpected, ..
+            } => ConfigGetError::Type {
+                name: args.name.to_string(),
+                error: format!("Expected a value convertible to a string, but is {unexpected}")
+                    .into(),
+                source_path: origin.map(PathBuf::from),
             }
-            if let Some(origin) = origin {
-                write!(buf, " in {origin}").unwrap();
-            }
-            config_error(buf)
+            .into(),
+            err => err.into(),
         }
-        err => err.into(),
     })?;
     writeln!(ui.stdout(), "{stringified}")?;
     Ok(())
diff --git a/cli/src/commands/git/fetch.rs b/cli/src/commands/git/fetch.rs
index 9ec64b233b..bf1226d436 100644
--- a/cli/src/commands/git/fetch.rs
+++ b/cli/src/commands/git/fetch.rs
@@ -14,7 +14,7 @@
 
 use clap_complete::ArgValueCandidates;
 use itertools::Itertools;
-use jj_lib::config::ConfigResultExt as _;
+use jj_lib::config::ConfigGetResultExt as _;
 use jj_lib::repo::Repo;
 use jj_lib::settings::UserSettings;
 use jj_lib::str_util::StringPattern;
diff --git a/cli/src/commands/git/push.rs b/cli/src/commands/git/push.rs
index bf3d8ea9e7..d835023940 100644
--- a/cli/src/commands/git/push.rs
+++ b/cli/src/commands/git/push.rs
@@ -21,7 +21,7 @@ use clap::ArgGroup;
 use clap_complete::ArgValueCandidates;
 use itertools::Itertools;
 use jj_lib::backend::CommitId;
-use jj_lib::config::ConfigResultExt as _;
+use jj_lib::config::ConfigGetResultExt as _;
 use jj_lib::git;
 use jj_lib::git::GitBranchPushTargets;
 use jj_lib::git::GitPushError;
diff --git a/cli/src/commands/log.rs b/cli/src/commands/log.rs
index 2009d9dd5f..5d514cfc83 100644
--- a/cli/src/commands/log.rs
+++ b/cli/src/commands/log.rs
@@ -14,8 +14,8 @@
 
 use clap_complete::ArgValueCandidates;
 use jj_lib::backend::CommitId;
-use jj_lib::config::ConfigError;
-use jj_lib::config::ConfigResultExt as _;
+use jj_lib::config::ConfigGetError;
+use jj_lib::config::ConfigGetResultExt as _;
 use jj_lib::graph::GraphEdgeType;
 use jj_lib::graph::ReverseGraphIterator;
 use jj_lib::graph::TopoGroupedGraphIterator;
@@ -331,7 +331,7 @@ pub(crate) fn cmd_log(
 pub fn get_node_template(
     style: GraphStyle,
     settings: &UserSettings,
-) -> Result<String, ConfigError> {
+) -> Result<String, ConfigGetError> {
     let symbol = settings.get_string("templates.log_node").optional()?;
     let default = if style.is_ascii() {
         "builtin_log_node_ascii"
diff --git a/cli/src/commands/operation/log.rs b/cli/src/commands/operation/log.rs
index 31d848c202..7d5d245c45 100644
--- a/cli/src/commands/operation/log.rs
+++ b/cli/src/commands/operation/log.rs
@@ -15,8 +15,8 @@
 use std::slice;
 
 use itertools::Itertools as _;
-use jj_lib::config::ConfigError;
-use jj_lib::config::ConfigResultExt as _;
+use jj_lib::config::ConfigGetError;
+use jj_lib::config::ConfigGetResultExt as _;
 use jj_lib::op_walk;
 use jj_lib::operation::Operation;
 use jj_lib::repo::RepoLoader;
@@ -247,7 +247,7 @@ fn do_op_log(
     Ok(())
 }
 
-fn get_node_template(style: GraphStyle, settings: &UserSettings) -> Result<String, ConfigError> {
+fn get_node_template(style: GraphStyle, settings: &UserSettings) -> Result<String, ConfigGetError> {
     let symbol = settings.get_string("templates.op_log_node").optional()?;
     let default = if style.is_ascii() {
         "builtin_op_log_node_ascii"
diff --git a/cli/src/diff_util.rs b/cli/src/diff_util.rs
index 77187caccb..d6a5e9e1f1 100644
--- a/cli/src/diff_util.rs
+++ b/cli/src/diff_util.rs
@@ -32,8 +32,8 @@ use jj_lib::backend::CommitId;
 use jj_lib::backend::CopyRecord;
 use jj_lib::backend::TreeValue;
 use jj_lib::commit::Commit;
-use jj_lib::config::ConfigError;
-use jj_lib::config::ConfigResultExt as _;
+use jj_lib::config::ConfigGetError;
+use jj_lib::config::ConfigGetResultExt as _;
 use jj_lib::conflicts::materialize_merge_result_to_bytes;
 use jj_lib::conflicts::materialized_diff_stream;
 use jj_lib::conflicts::ConflictMarkerStyle;
@@ -147,7 +147,7 @@ pub enum DiffFormat {
 pub fn diff_formats_for(
     settings: &UserSettings,
     args: &DiffFormatArgs,
-) -> Result<Vec<DiffFormat>, ConfigError> {
+) -> Result<Vec<DiffFormat>, ConfigGetError> {
     let formats = diff_formats_from_args(settings, args)?;
     if formats.is_empty() {
         Ok(vec![default_diff_format(settings, args)?])
@@ -162,7 +162,7 @@ pub fn diff_formats_for_log(
     settings: &UserSettings,
     args: &DiffFormatArgs,
     patch: bool,
-) -> Result<Vec<DiffFormat>, ConfigError> {
+) -> Result<Vec<DiffFormat>, ConfigGetError> {
     let mut formats = diff_formats_from_args(settings, args)?;
     // --patch implies default if no format other than --summary is specified
     if patch && matches!(formats.as_slice(), [] | [DiffFormat::Summary]) {
@@ -175,7 +175,7 @@ pub fn diff_formats_for_log(
 fn diff_formats_from_args(
     settings: &UserSettings,
     args: &DiffFormatArgs,
-) -> Result<Vec<DiffFormat>, ConfigError> {
+) -> Result<Vec<DiffFormat>, ConfigGetError> {
     let mut formats = Vec::new();
     if args.summary {
         formats.push(DiffFormat::Summary);
@@ -209,7 +209,7 @@ fn diff_formats_from_args(
 fn default_diff_format(
     settings: &UserSettings,
     args: &DiffFormatArgs,
-) -> Result<DiffFormat, ConfigError> {
+) -> Result<DiffFormat, ConfigGetError> {
     if let Some(args) = settings.get("ui.diff.tool").optional()? {
         // External "tool" overrides the internal "format" option.
         let tool = if let CommandNameAndArgs::String(name) = &args {
@@ -243,7 +243,11 @@ fn default_diff_format(
             let options = DiffStatOptions::from_args(args);
             Ok(DiffFormat::Stat(Box::new(options)))
         }
-        _ => Err(ConfigError::Message(format!("invalid diff format: {name}"))),
+        _ => Err(ConfigGetError::Type {
+            name: "ui.diff.format".to_owned(),
+            error: format!("Invalid diff format: {name}").into(),
+            source_path: None,
+        }),
     }
 }
 
@@ -544,15 +548,16 @@ impl ColorWordsDiffOptions {
     fn from_settings_and_args(
         settings: &UserSettings,
         args: &DiffFormatArgs,
-    ) -> Result<Self, ConfigError> {
+    ) -> Result<Self, ConfigGetError> {
         let max_inline_alternation = {
-            let key = "diff.color-words.max-inline-alternation";
-            match settings.get_int(key)? {
+            let name = "diff.color-words.max-inline-alternation";
+            match settings.get_int(name)? {
                 -1 => None, // unlimited
-                n => Some(
-                    usize::try_from(n)
-                        .map_err(|err| ConfigError::Message(format!("invalid {key}: {err}")))?,
-                ),
+                n => Some(usize::try_from(n).map_err(|err| ConfigGetError::Type {
+                    name: name.to_owned(),
+                    error: err.into(),
+                    source_path: None,
+                })?),
             }
         };
         let context = args
@@ -1252,7 +1257,7 @@ impl UnifiedDiffOptions {
     fn from_settings_and_args(
         settings: &UserSettings,
         args: &DiffFormatArgs,
-    ) -> Result<Self, ConfigError> {
+    ) -> Result<Self, ConfigGetError> {
         let context = args
             .context
             .map_or_else(|| settings.get("diff.git.context"), Ok)?;
diff --git a/cli/src/formatter.rs b/cli/src/formatter.rs
index 9b88a8fa37..d2d15c24dd 100644
--- a/cli/src/formatter.rs
+++ b/cli/src/formatter.rs
@@ -29,7 +29,7 @@ use crossterm::style::SetAttribute;
 use crossterm::style::SetBackgroundColor;
 use crossterm::style::SetForegroundColor;
 use itertools::Itertools;
-use jj_lib::config::ConfigError;
+use jj_lib::config::ConfigGetError;
 use jj_lib::config::StackedConfig;
 
 // Lets the caller label strings and translates the labels to colors
@@ -160,7 +160,7 @@ impl FormatterFactory {
         FormatterFactory { kind }
     }
 
-    pub fn color(config: &StackedConfig, debug: bool) -> Result<Self, ConfigError> {
+    pub fn color(config: &StackedConfig, debug: bool) -> Result<Self, ConfigGetError> {
         let rules = Arc::new(rules_from_config(config)?);
         let kind = FormatterFactoryKind::Color { rules, debug };
         Ok(FormatterFactory { kind })
@@ -297,7 +297,11 @@ impl<W: Write> ColorFormatter<W> {
         }
     }
 
-    pub fn for_config(output: W, config: &StackedConfig, debug: bool) -> Result<Self, ConfigError> {
+    pub fn for_config(
+        output: W,
+        config: &StackedConfig,
+        debug: bool,
+    ) -> Result<Self, ConfigGetError> {
         let rules = rules_from_config(config)?;
         Ok(Self::new(output, Arc::new(rules), debug))
     }
@@ -401,10 +405,15 @@ impl<W: Write> ColorFormatter<W> {
     }
 }
 
-fn rules_from_config(config: &StackedConfig) -> Result<Rules, ConfigError> {
+fn rules_from_config(config: &StackedConfig) -> Result<Rules, ConfigGetError> {
     let mut result = vec![];
     let table = config.get_table("colors")?;
     for (key, value) in table {
+        let to_config_err = |message: String| ConfigGetError::Type {
+            name: format!("colors.'{key}'"),
+            error: message.into(),
+            source_path: None,
+        };
         let labels = key
             .split_whitespace()
             .map(ToString::to_string)
@@ -412,7 +421,7 @@ fn rules_from_config(config: &StackedConfig) -> Result<Rules, ConfigError> {
         match value.kind {
             config::ValueKind::String(color_name) => {
                 let style = Style {
-                    fg_color: Some(color_for_name_or_hex(&color_name)?),
+                    fg_color: Some(color_for_name_or_hex(&color_name).map_err(to_config_err)?),
                     bg_color: None,
                     bold: None,
                     underlined: None,
@@ -423,12 +432,14 @@ fn rules_from_config(config: &StackedConfig) -> Result<Rules, ConfigError> {
                 let mut style = Style::default();
                 if let Some(value) = style_table.get("fg") {
                     if let config::ValueKind::String(color_name) = &value.kind {
-                        style.fg_color = Some(color_for_name_or_hex(color_name)?);
+                        style.fg_color =
+                            Some(color_for_name_or_hex(color_name).map_err(to_config_err)?);
                     }
                 }
                 if let Some(value) = style_table.get("bg") {
                     if let config::ValueKind::String(color_name) = &value.kind {
-                        style.bg_color = Some(color_for_name_or_hex(color_name)?);
+                        style.bg_color =
+                            Some(color_for_name_or_hex(color_name).map_err(to_config_err)?);
                     }
                 }
                 if let Some(value) = style_table.get("bold") {
@@ -449,7 +460,7 @@ fn rules_from_config(config: &StackedConfig) -> Result<Rules, ConfigError> {
     Ok(result)
 }
 
-fn color_for_name_or_hex(name_or_hex: &str) -> Result<Color, ConfigError> {
+fn color_for_name_or_hex(name_or_hex: &str) -> Result<Color, String> {
     match name_or_hex {
         "default" => Ok(Color::Reset),
         "black" => Ok(Color::Black),
@@ -468,8 +479,7 @@ fn color_for_name_or_hex(name_or_hex: &str) -> Result<Color, ConfigError> {
         "bright magenta" => Ok(Color::Magenta),
         "bright cyan" => Ok(Color::Cyan),
         "bright white" => Ok(Color::White),
-        _ => color_for_hex(name_or_hex)
-            .ok_or_else(|| ConfigError::Message(format!("invalid color: {name_or_hex}"))),
+        _ => color_for_hex(name_or_hex).ok_or_else(|| format!("Invalid color: {name_or_hex}")),
     }
 }
 
@@ -699,6 +709,7 @@ fn write_sanitized(output: &mut impl Write, buf: &[u8]) -> Result<(), Error> {
 
 #[cfg(test)]
 mod tests {
+    use std::error::Error as _;
     use std::str;
 
     use indoc::indoc;
@@ -1018,11 +1029,9 @@ mod tests {
         "#,
         );
         let mut output: Vec<u8> = vec![];
-        let err = ColorFormatter::for_config(&mut output, &config, false)
-            .unwrap_err()
-            .to_string();
-        insta::assert_snapshot!(err,
-        @"invalid color: bloo");
+        let err = ColorFormatter::for_config(&mut output, &config, false).unwrap_err();
+        insta::assert_snapshot!(err, @"Invalid type or value for colors.'outer inner'");
+        insta::assert_snapshot!(err.source().unwrap(), @"Invalid color: bloo");
     }
 
     #[test]
@@ -1035,11 +1044,9 @@ mod tests {
             "##,
         );
         let mut output: Vec<u8> = vec![];
-        let err = ColorFormatter::for_config(&mut output, &config, false)
-            .unwrap_err()
-            .to_string();
-        insta::assert_snapshot!(err,
-            @"invalid color: #ffgggg");
+        let err = ColorFormatter::for_config(&mut output, &config, false).unwrap_err();
+        insta::assert_snapshot!(err, @"Invalid type or value for colors.'outer inner'");
+        insta::assert_snapshot!(err.source().unwrap(), @"Invalid color: #ffgggg");
     }
 
     #[test]
diff --git a/cli/src/graphlog.rs b/cli/src/graphlog.rs
index 550592b02e..de168e43dc 100644
--- a/cli/src/graphlog.rs
+++ b/cli/src/graphlog.rs
@@ -17,7 +17,7 @@ use std::io;
 use std::io::Write;
 
 use itertools::Itertools;
-use jj_lib::config::ConfigError;
+use jj_lib::config::ConfigGetError;
 use jj_lib::settings::UserSettings;
 use renderdag::Ancestor;
 use renderdag::GraphRowRenderer;
@@ -113,7 +113,7 @@ pub enum GraphStyle {
 }
 
 impl GraphStyle {
-    pub fn from_settings(settings: &UserSettings) -> Result<Self, ConfigError> {
+    pub fn from_settings(settings: &UserSettings) -> Result<Self, ConfigGetError> {
         settings.get("ui.graph.style")
     }
 
diff --git a/cli/src/merge_tools/mod.rs b/cli/src/merge_tools/mod.rs
index 83002607b7..25d829936a 100644
--- a/cli/src/merge_tools/mod.rs
+++ b/cli/src/merge_tools/mod.rs
@@ -19,9 +19,9 @@ mod external;
 use std::sync::Arc;
 
 use jj_lib::backend::MergedTreeId;
-use jj_lib::config::ConfigError;
+use jj_lib::config::ConfigGetError;
+use jj_lib::config::ConfigGetResultExt as _;
 use jj_lib::config::ConfigNamePathBuf;
-use jj_lib::config::ConfigResultExt as _;
 use jj_lib::conflicts::extract_as_single_hunk;
 use jj_lib::conflicts::ConflictMarkerStyle;
 use jj_lib::gitignore::GitIgnoreFile;
@@ -62,7 +62,7 @@ pub enum DiffEditError {
     #[error("Failed to snapshot changes")]
     Snapshot(#[from] SnapshotError),
     #[error(transparent)]
-    Config(#[from] ConfigError),
+    Config(#[from] ConfigGetError),
 }
 
 #[derive(Debug, Error)]
@@ -104,7 +104,7 @@ pub enum ConflictResolveError {
 #[derive(Debug, Error)]
 pub enum MergeToolConfigError {
     #[error(transparent)]
-    Config(#[from] ConfigError),
+    Config(#[from] ConfigGetError),
     #[error("The tool `{tool_name}` cannot be used as a merge tool with `jj resolve`")]
     MergeArgsNotConfigured { tool_name: String },
 }
@@ -127,7 +127,7 @@ fn editor_args_from_settings(
     ui: &Ui,
     settings: &UserSettings,
     key: &'static str,
-) -> Result<CommandNameAndArgs, ConfigError> {
+) -> Result<CommandNameAndArgs, ConfigGetError> {
     // TODO: Make this configuration have a table of possible editors and detect the
     // best one here.
     if let Some(args) = settings.get(key).optional()? {
@@ -146,7 +146,10 @@ fn editor_args_from_settings(
 
 /// Resolves builtin merge tool name or loads external tool options from
 /// `[merge-tools.<name>]`.
-fn get_tool_config(settings: &UserSettings, name: &str) -> Result<Option<MergeTool>, ConfigError> {
+fn get_tool_config(
+    settings: &UserSettings,
+    name: &str,
+) -> Result<Option<MergeTool>, ConfigGetError> {
     if name == BUILTIN_EDITOR_NAME {
         Ok(Some(MergeTool::Builtin))
     } else {
@@ -158,14 +161,9 @@ fn get_tool_config(settings: &UserSettings, name: &str) -> Result<Option<MergeTo
 pub fn get_external_tool_config(
     settings: &UserSettings,
     name: &str,
-) -> Result<Option<ExternalMergeTool>, ConfigError> {
+) -> Result<Option<ExternalMergeTool>, ConfigGetError> {
     let full_name = ConfigNamePathBuf::from_iter(["merge-tools", name]);
-    let Some(mut tool) = settings
-        .get::<ExternalMergeTool>(&full_name)
-        .optional()
-        // add config key, deserialize error is otherwise unclear
-        .map_err(|e| ConfigError::Message(format!("{full_name}: {e}")))?
-    else {
+    let Some(mut tool) = settings.get::<ExternalMergeTool>(&full_name).optional()? else {
         return Ok(None);
     };
     if tool.program.is_empty() {
diff --git a/cli/src/revset_util.rs b/cli/src/revset_util.rs
index 42a206b97f..32af07a205 100644
--- a/cli/src/revset_util.rs
+++ b/cli/src/revset_util.rs
@@ -21,6 +21,7 @@ use std::sync::Arc;
 use itertools::Itertools as _;
 use jj_lib::backend::CommitId;
 use jj_lib::commit::Commit;
+use jj_lib::config::ConfigGetError;
 use jj_lib::config::ConfigNamePathBuf;
 use jj_lib::config::ConfigSource;
 use jj_lib::config::StackedConfig;
@@ -174,8 +175,16 @@ pub fn load_revset_aliases(
         let table = match layer.look_up_table(&table_name) {
             Ok(Some(table)) => table,
             Ok(None) => continue,
-            // TODO: rewrite error construction after migrating to toml_edit
-            Err(item) => return Err(item.clone().into_table().unwrap_err().into()),
+            Err(item) => {
+                // TODO: rewrite error construction after migrating to toml_edit
+                let error = item.clone().into_table().unwrap_err();
+                return Err(ConfigGetError::Type {
+                    name: table_name.to_string(),
+                    error: error.into(),
+                    source_path: layer.path.clone(),
+                }
+                .into());
+            }
         };
         // TODO: remove sorting after migrating to toml_edit
         for (decl, value) in table.iter().sorted_by_key(|&(decl, _)| decl) {
diff --git a/cli/src/ui.rs b/cli/src/ui.rs
index 333bce96a1..cd4ec6fb2f 100644
--- a/cli/src/ui.rs
+++ b/cli/src/ui.rs
@@ -32,13 +32,12 @@ use std::thread::JoinHandle;
 
 use indoc::indoc;
 use itertools::Itertools as _;
-use jj_lib::config::ConfigError;
+use jj_lib::config::ConfigGetError;
 use jj_lib::config::StackedConfig;
 use minus::MinusError;
 use minus::Pager as MinusPager;
 use tracing::instrument;
 
-use crate::command_error::config_error_with_message;
 use crate::command_error::CommandError;
 use crate::config::CommandNameAndArgs;
 use crate::formatter::Formatter;
@@ -313,7 +312,7 @@ fn color_setting(config: &StackedConfig) -> ColorChoice {
 fn prepare_formatter_factory(
     config: &StackedConfig,
     stdout: &Stdout,
-) -> Result<FormatterFactory, ConfigError> {
+) -> Result<FormatterFactory, ConfigGetError> {
     let terminal = stdout.is_terminal();
     let (color, debug) = match color_setting(config) {
         ColorChoice::Always => (true, false),
@@ -344,16 +343,12 @@ pub enum PaginationChoice {
     Auto,
 }
 
-fn pagination_setting(config: &StackedConfig) -> Result<PaginationChoice, CommandError> {
-    config
-        .get::<PaginationChoice>("ui.paginate")
-        .map_err(|err| config_error_with_message("Invalid `ui.paginate`", err))
+fn pagination_setting(config: &StackedConfig) -> Result<PaginationChoice, ConfigGetError> {
+    config.get::<PaginationChoice>("ui.paginate")
 }
 
-fn pager_setting(config: &StackedConfig) -> Result<CommandNameAndArgs, CommandError> {
-    config
-        .get::<CommandNameAndArgs>("ui.pager")
-        .map_err(|err| config_error_with_message("Invalid `ui.pager`", err))
+fn pager_setting(config: &StackedConfig) -> Result<CommandNameAndArgs, ConfigGetError> {
+    config.get::<CommandNameAndArgs>("ui.pager")
 }
 
 impl Ui {
diff --git a/cli/tests/test_config_command.rs b/cli/tests/test_config_command.rs
index ede468a359..06fd7b08c5 100644
--- a/cli/tests/test_config_command.rs
+++ b/cli/tests/test_config_command.rs
@@ -820,10 +820,10 @@ fn test_config_get() {
     );
 
     let stdout = test_env.jj_cmd_failure(test_env.env_root(), &["config", "get", "nonexistent"]);
-    insta::assert_snapshot!(stdout, @r###"
-    Config error: configuration property "nonexistent" not found
+    insta::assert_snapshot!(stdout, @r"
+    Config error: Value not found for nonexistent
     For help, see https://martinvonz.github.io/jj/latest/config/.
-    "###);
+    ");
 
     let stdout = test_env.jj_cmd_success(test_env.env_root(), &["config", "get", "table.string"]);
     insta::assert_snapshot!(stdout, @r###"
@@ -837,15 +837,18 @@ fn test_config_get() {
 
     let stdout = test_env.jj_cmd_failure(test_env.env_root(), &["config", "get", "table.list"]);
     insta::assert_snapshot!(stdout.replace('\\', "/"), @r"
-    Config error: invalid type: sequence, expected a value convertible to a string in config/config0002.toml
+    Config error: Invalid type or value for table.list
+    Caused by: Expected a value convertible to a string, but is sequence
+    Hint: Check the config file: config/config0002.toml
     For help, see https://martinvonz.github.io/jj/latest/config/.
     ");
 
     let stdout = test_env.jj_cmd_failure(test_env.env_root(), &["config", "get", "table"]);
-    insta::assert_snapshot!(stdout, @r###"
-    Config error: invalid type: map, expected a value convertible to a string
+    insta::assert_snapshot!(stdout, @r"
+    Config error: Invalid type or value for table
+    Caused by: Expected a value convertible to a string, but is map
     For help, see https://martinvonz.github.io/jj/latest/config/.
-    "###);
+    ");
 
     let stdout =
         test_env.jj_cmd_success(test_env.env_root(), &["config", "get", "table.overridden"]);
@@ -896,10 +899,10 @@ fn test_config_path_syntax() {
     Warning: No matching config key for a.'b()'.x
     "###);
     let stderr = test_env.jj_cmd_failure(test_env.env_root(), &["config", "get", "a.'b()'.x"]);
-    insta::assert_snapshot!(stderr, @r###"
-    Config error: configuration property "a.'b()'.x" not found
+    insta::assert_snapshot!(stderr, @r"
+    Config error: Value not found for a.'b()'.x
     For help, see https://martinvonz.github.io/jj/latest/config/.
-    "###);
+    ");
 
     // "-" and "_" are valid TOML keys
     let stdout = test_env.jj_cmd_success(test_env.env_root(), &["config", "list", "-"]);
@@ -970,13 +973,12 @@ fn test_config_show_paths() {
         &["config", "set", "--user", "ui.paginate", ":builtin"],
     );
     let stderr = test_env.jj_cmd_failure(test_env.env_root(), &["st"]);
-    insta::assert_snapshot!(stderr, @r###"
-    Config error: Invalid `ui.paginate`
+    insta::assert_snapshot!(stderr, @r"
+    Config error: Invalid type or value for ui.paginate
     Caused by: enum PaginationChoice does not have variant constructor :builtin
-    Hint: Check the following config files:
-    - $TEST_ENV/config/config.toml
+    Hint: Check the config file: $TEST_ENV/config/config.toml
     For help, see https://martinvonz.github.io/jj/latest/config/.
-    "###);
+    ");
 }
 
 #[test]
diff --git a/cli/tests/test_global_opts.rs b/cli/tests/test_global_opts.rs
index 475d388dfa..3f7b476ed0 100644
--- a/cli/tests/test_global_opts.rs
+++ b/cli/tests/test_global_opts.rs
@@ -604,7 +604,8 @@ fn test_invalid_config_value() {
         &["status", "--config-toml=snapshot.auto-track=[0]"],
     );
     insta::assert_snapshot!(stderr, @r"
-    Config error: invalid type: sequence, expected a string for key `snapshot.auto-track`
+    Config error: Invalid type or value for snapshot.auto-track
+    Caused by: invalid type: sequence, expected a string
     For help, see https://martinvonz.github.io/jj/latest/config/.
     ");
 }
diff --git a/cli/tests/test_log_command.rs b/cli/tests/test_log_command.rs
index 3bf63a9cc5..48e7c706c3 100644
--- a/cli/tests/test_log_command.rs
+++ b/cli/tests/test_log_command.rs
@@ -1324,10 +1324,11 @@ fn test_graph_styles() {
         &repo_path,
         &["log", "--config-toml=ui.graph.style='unknown'"],
     );
-    insta::assert_snapshot!(stderr, @r###"
-    Config error: enum GraphStyle does not have variant constructor unknown
+    insta::assert_snapshot!(stderr, @r"
+    Config error: Invalid type or value for ui.graph.style
+    Caused by: enum GraphStyle does not have variant constructor unknown
     For help, see https://martinvonz.github.io/jj/latest/config/.
-    "###);
+    ");
 }
 
 #[test]
diff --git a/lib/src/config.rs b/lib/src/config.rs
index e69cb8333b..382fd33ae6 100644
--- a/lib/src/config.rs
+++ b/lib/src/config.rs
@@ -15,6 +15,7 @@
 //! Configuration store helpers.
 
 use std::borrow::Borrow;
+use std::convert::Infallible;
 use std::fmt;
 use std::ops::Range;
 use std::path::Path;
@@ -24,6 +25,7 @@ use std::str::FromStr;
 
 use itertools::Itertools as _;
 use serde::Deserialize;
+use thiserror::Error;
 
 use crate::file_util::IoResultExt as _;
 
@@ -36,17 +38,39 @@ pub type ConfigValue = config::Value;
 // TODO: will be replaced with our custom error type
 pub type ConfigError = config::ConfigError;
 
-/// Extension methods for `Result<T, ConfigError>`.
-pub trait ConfigResultExt<T> {
+/// Error that can occur when looking up config variable.
+#[derive(Debug, Error)]
+pub enum ConfigGetError {
+    /// Config value is not set.
+    #[error("Value not found for {name}")]
+    NotFound {
+        /// Dotted config name path.
+        name: String,
+    },
+    /// Config value cannot be converted to the expected type.
+    #[error("Invalid type or value for {name}")]
+    Type {
+        /// Dotted config name path.
+        name: String,
+        /// Source error.
+        #[source]
+        error: Box<dyn std::error::Error + Send + Sync>,
+        /// Source file path where the value is defined.
+        source_path: Option<PathBuf>,
+    },
+}
+
+/// Extension methods for `Result<T, ConfigGetError>`.
+pub trait ConfigGetResultExt<T> {
     /// Converts `NotFound` error to `Ok(None)`, leaving other errors.
-    fn optional(self) -> Result<Option<T>, ConfigError>;
+    fn optional(self) -> Result<Option<T>, ConfigGetError>;
 }
 
-impl<T> ConfigResultExt<T> for Result<T, ConfigError> {
-    fn optional(self) -> Result<Option<T>, ConfigError> {
+impl<T> ConfigGetResultExt<T> for Result<T, ConfigGetError> {
+    fn optional(self) -> Result<Option<T>, ConfigGetError> {
         match self {
             Ok(value) => Ok(Some(value)),
-            Err(ConfigError::NotFound(_)) => Ok(None),
+            Err(ConfigGetError::NotFound { .. }) => Ok(None),
             Err(err) => Err(err),
         }
     }
@@ -396,37 +420,42 @@ impl StackedConfig {
     pub fn get<'de, T: Deserialize<'de>>(
         &self,
         name: impl ToConfigNamePath,
-    ) -> Result<T, ConfigError> {
+    ) -> Result<T, ConfigGetError> {
         self.get_item_with(name, T::deserialize)
     }
 
     /// Looks up value from all layers, merges sub fields as needed.
-    pub fn get_value(&self, name: impl ToConfigNamePath) -> Result<ConfigValue, ConfigError> {
-        self.get_item_with(name, Ok)
+    pub fn get_value(&self, name: impl ToConfigNamePath) -> Result<ConfigValue, ConfigGetError> {
+        self.get_item_with::<_, Infallible>(name, Ok)
     }
 
     /// Looks up sub table from all layers, merges fields as needed.
     // TODO: redesign this to attach better error indication?
-    pub fn get_table(&self, name: impl ToConfigNamePath) -> Result<ConfigTable, ConfigError> {
+    pub fn get_table(&self, name: impl ToConfigNamePath) -> Result<ConfigTable, ConfigGetError> {
         self.get(name)
     }
 
-    fn get_item_with<T>(
+    fn get_item_with<T, E: Into<Box<dyn std::error::Error + Send + Sync>>>(
         &self,
         name: impl ToConfigNamePath,
-        convert: impl FnOnce(ConfigValue) -> Result<T, ConfigError>,
-    ) -> Result<T, ConfigError> {
+        convert: impl FnOnce(ConfigValue) -> Result<T, E>,
+    ) -> Result<T, ConfigGetError> {
         let name = name.into_name_path();
         let name = name.borrow();
-        let (item, _layer_index) = get_merged_item(&self.layers, name)
-            .ok_or_else(|| ConfigError::NotFound(name.to_string()))?;
-        // TODO: Add source type/path to the error message. If the value is
-        // a table, the error might come from lower layers. We cannot report
-        // precise source information in that case. However, toml_edit captures
-        // dotted keys in the error object. If the keys field were public, we
-        // can look up the source information. This is probably simpler than
-        // reimplementing Deserializer.
-        convert(item).map_err(|err| err.extend_with_key(&name.to_string()))
+        let (item, layer_index) =
+            get_merged_item(&self.layers, name).ok_or_else(|| ConfigGetError::NotFound {
+                name: name.to_string(),
+            })?;
+        // If the value is a table, the error might come from lower layers. We
+        // cannot report precise source information in that case. However,
+        // toml_edit captures dotted keys in the error object. If the keys field
+        // were public, we can look up the source information. This is probably
+        // simpler than reimplementing Deserializer.
+        convert(item).map_err(|err| ConfigGetError::Type {
+            name: name.to_string(),
+            error: err.into(),
+            source_path: self.layers[layer_index].path.clone(),
+        })
     }
 }
 
@@ -587,19 +616,19 @@ mod tests {
         // Table "a.b" exists, but key doesn't
         assert_matches!(
             config.get::<String>("a.b.missing"),
-            Err(ConfigError::NotFound(name)) if name == "a.b.missing"
+            Err(ConfigGetError::NotFound { name }) if name == "a.b.missing"
         );
 
         // Node "a.b.c" is not a table
         assert_matches!(
             config.get::<String>("a.b.c.d"),
-            Err(ConfigError::NotFound(name)) if name == "a.b.c.d"
+            Err(ConfigGetError::NotFound { name }) if name == "a.b.c.d"
         );
 
         // Type error
         assert_matches!(
             config.get::<String>("a.b"),
-            Err(ConfigError::Type { key: Some(name), .. }) if name == "a.b"
+            Err(ConfigGetError::Type { name, .. }) if name == "a.b"
         );
     }
 
@@ -618,7 +647,7 @@ mod tests {
 
         assert_matches!(
             config.get::<String>("a.b.c"),
-            Err(ConfigError::NotFound(name)) if name == "a.b.c"
+            Err(ConfigGetError::NotFound { name }) if name == "a.b.c"
         );
     }
 
diff --git a/lib/src/fsmonitor.rs b/lib/src/fsmonitor.rs
index 767620da27..9fa864f457 100644
--- a/lib/src/fsmonitor.rs
+++ b/lib/src/fsmonitor.rs
@@ -24,8 +24,8 @@
 
 use std::path::PathBuf;
 
-use crate::config::ConfigError;
-use crate::config::ConfigResultExt as _;
+use crate::config::ConfigGetError;
+use crate::config::ConfigGetResultExt as _;
 use crate::settings::UserSettings;
 
 /// Config for Watchman filesystem monitor (<https://facebook.github.io/watchman/>).
@@ -58,8 +58,9 @@ pub enum FsmonitorSettings {
 
 impl FsmonitorSettings {
     /// Creates an `FsmonitorSettings` from a `config`.
-    pub fn from_settings(settings: &UserSettings) -> Result<FsmonitorSettings, ConfigError> {
-        match settings.get_string("core.fsmonitor") {
+    pub fn from_settings(settings: &UserSettings) -> Result<FsmonitorSettings, ConfigGetError> {
+        let name = "core.fsmonitor";
+        match settings.get_string(name) {
             Ok(s) => match s.as_str() {
                 "watchman" => Ok(Self::Watchman(WatchmanConfig {
                     register_trigger: settings
@@ -67,15 +68,19 @@ impl FsmonitorSettings {
                         .optional()?
                         .unwrap_or_default(),
                 })),
-                "test" => Err(ConfigError::Message(
-                    "cannot use test fsmonitor in real repository".to_string(),
-                )),
+                "test" => Err(ConfigGetError::Type {
+                    name: name.to_owned(),
+                    error: "Cannot use test fsmonitor in real repository".into(),
+                    source_path: None,
+                }),
                 "none" => Ok(Self::None),
-                other => Err(ConfigError::Message(format!(
-                    "unknown fsmonitor kind: {other}",
-                ))),
+                other => Err(ConfigGetError::Type {
+                    name: name.to_owned(),
+                    error: format!("Unknown fsmonitor kind: {other}").into(),
+                    source_path: None,
+                }),
             },
-            Err(ConfigError::NotFound(_)) => Ok(Self::None),
+            Err(ConfigGetError::NotFound { .. }) => Ok(Self::None),
             Err(err) => Err(err),
         }
     }
diff --git a/lib/src/gpg_signing.rs b/lib/src/gpg_signing.rs
index 654b4ba680..6ba6dfb2f0 100644
--- a/lib/src/gpg_signing.rs
+++ b/lib/src/gpg_signing.rs
@@ -25,8 +25,8 @@ use std::str;
 
 use thiserror::Error;
 
-use crate::config::ConfigError;
-use crate::config::ConfigResultExt as _;
+use crate::config::ConfigGetError;
+use crate::config::ConfigGetResultExt as _;
 use crate::settings::UserSettings;
 use crate::signing::SigStatus;
 use crate::signing::SignError;
@@ -146,7 +146,7 @@ impl GpgBackend {
         self
     }
 
-    pub fn from_settings(settings: &UserSettings) -> Result<Self, ConfigError> {
+    pub fn from_settings(settings: &UserSettings) -> Result<Self, ConfigGetError> {
         let program = settings
             .get_string("signing.backends.gpg.program")
             .optional()?
diff --git a/lib/src/settings.rs b/lib/src/settings.rs
index 6968690db4..b15bf5b1b5 100644
--- a/lib/src/settings.rs
+++ b/lib/src/settings.rs
@@ -27,8 +27,8 @@ use crate::backend::ChangeId;
 use crate::backend::Commit;
 use crate::backend::Signature;
 use crate::backend::Timestamp;
-use crate::config::ConfigError;
-use crate::config::ConfigResultExt as _;
+use crate::config::ConfigGetError;
+use crate::config::ConfigGetResultExt as _;
 use crate::config::ConfigTable;
 use crate::config::ConfigValue;
 use crate::config::StackedConfig;
@@ -166,7 +166,7 @@ impl UserSettings {
         self.get_string("user.email").unwrap_or_default()
     }
 
-    pub fn fsmonitor_settings(&self) -> Result<FsmonitorSettings, ConfigError> {
+    pub fn fsmonitor_settings(&self) -> Result<FsmonitorSettings, ConfigGetError> {
         FsmonitorSettings::from_settings(self)
     }
 
@@ -234,14 +234,14 @@ impl UserSettings {
         GitSettings::from_settings(self)
     }
 
-    pub fn max_new_file_size(&self) -> Result<u64, ConfigError> {
+    pub fn max_new_file_size(&self) -> Result<u64, ConfigGetError> {
         let cfg = self
             .get::<HumanByteSize>("snapshot.max-new-file-size")
             .map(|x| x.0);
         match cfg {
             Ok(0) => Ok(u64::MAX),
             x @ Ok(_) => x,
-            Err(ConfigError::NotFound(_)) => Ok(1024 * 1024),
+            Err(ConfigGetError::NotFound { .. }) => Ok(1024 * 1024),
             e @ Err(_) => e,
         }
     }
@@ -257,7 +257,7 @@ impl UserSettings {
         SignSettings::from_settings(self)
     }
 
-    pub fn conflict_marker_style(&self) -> Result<ConflictMarkerStyle, ConfigError> {
+    pub fn conflict_marker_style(&self) -> Result<ConflictMarkerStyle, ConfigGetError> {
         Ok(self
             .get("ui.conflict-marker-style")
             .optional()?
@@ -271,32 +271,32 @@ impl UserSettings {
     pub fn get<'de, T: Deserialize<'de>>(
         &self,
         name: impl ToConfigNamePath,
-    ) -> Result<T, ConfigError> {
+    ) -> Result<T, ConfigGetError> {
         self.config.get(name)
     }
 
     /// Looks up string value by `name`.
-    pub fn get_string(&self, name: impl ToConfigNamePath) -> Result<String, ConfigError> {
+    pub fn get_string(&self, name: impl ToConfigNamePath) -> Result<String, ConfigGetError> {
         self.get(name)
     }
 
     /// Looks up integer value by `name`.
-    pub fn get_int(&self, name: impl ToConfigNamePath) -> Result<i64, ConfigError> {
+    pub fn get_int(&self, name: impl ToConfigNamePath) -> Result<i64, ConfigGetError> {
         self.get(name)
     }
 
     /// Looks up boolean value by `name`.
-    pub fn get_bool(&self, name: impl ToConfigNamePath) -> Result<bool, ConfigError> {
+    pub fn get_bool(&self, name: impl ToConfigNamePath) -> Result<bool, ConfigGetError> {
         self.get(name)
     }
 
     /// Looks up generic value by `name`.
-    pub fn get_value(&self, name: impl ToConfigNamePath) -> Result<ConfigValue, ConfigError> {
+    pub fn get_value(&self, name: impl ToConfigNamePath) -> Result<ConfigValue, ConfigGetError> {
         self.config.get_value(name)
     }
 
     /// Looks up sub table by `name`.
-    pub fn get_table(&self, name: impl ToConfigNamePath) -> Result<ConfigTable, ConfigError> {
+    pub fn get_table(&self, name: impl ToConfigNamePath) -> Result<ConfigTable, ConfigGetError> {
         self.config.get_table(name)
     }
 }
diff --git a/lib/src/signing.rs b/lib/src/signing.rs
index d0d594988e..6a23410b8e 100644
--- a/lib/src/signing.rs
+++ b/lib/src/signing.rs
@@ -22,7 +22,7 @@ use std::sync::RwLock;
 use thiserror::Error;
 
 use crate::backend::CommitId;
-use crate::config::ConfigError;
+use crate::config::ConfigGetError;
 use crate::gpg_signing::GpgBackend;
 use crate::settings::UserSettings;
 use crate::ssh_signing::SshBackend;
@@ -122,7 +122,7 @@ pub enum SignInitError {
     UnknownBackend(String),
     /// Failed to load backend configuration.
     #[error("Failed to configure signing backend")]
-    BackendConfig(#[source] ConfigError),
+    BackendConfig(#[source] ConfigGetError),
 }
 
 /// A enum that describes if a created/rewritten commit should be signed or not.
diff --git a/lib/src/ssh_signing.rs b/lib/src/ssh_signing.rs
index 554b2fd2a5..e19f489fbf 100644
--- a/lib/src/ssh_signing.rs
+++ b/lib/src/ssh_signing.rs
@@ -26,8 +26,8 @@ use std::process::Stdio;
 use either::Either;
 use thiserror::Error;
 
-use crate::config::ConfigError;
-use crate::config::ConfigResultExt as _;
+use crate::config::ConfigGetError;
+use crate::config::ConfigGetResultExt as _;
 use crate::settings::UserSettings;
 use crate::signing::SigStatus;
 use crate::signing::SignError;
@@ -119,7 +119,7 @@ impl SshBackend {
         }
     }
 
-    pub fn from_settings(settings: &UserSettings) -> Result<Self, ConfigError> {
+    pub fn from_settings(settings: &UserSettings) -> Result<Self, ConfigGetError> {
         let program = settings
             .get_string("signing.backends.ssh.program")
             .optional()?