diff --git a/crates/ty_project/src/metadata/options.rs b/crates/ty_project/src/metadata/options.rs
index bcd821c53d141..de9f70352de45 100644
--- a/crates/ty_project/src/metadata/options.rs
+++ b/crates/ty_project/src/metadata/options.rs
@@ -94,9 +94,23 @@ pub struct Options {
     #[serde(skip_serializing_if = "Option::is_none")]
     #[option_group]
     pub overrides: Option<OverridesOptions>,
+
+    /// Settings Failure Is Not An Error.
+    ///
+    /// This is used by the default database, which we are incentivized to make infallible,
+    /// while still trying to "do our best" to set things up properly where we can.
+    #[serde(default, skip)]
+    pub safe_mode: bool,
 }
 
 impl Options {
+    pub fn safe() -> Self {
+        Self {
+            safe_mode: true,
+            ..Self::default()
+        }
+    }
+
     pub fn from_toml_str(content: &str, source: ValueSource) -> Result<Self, TyTomlError> {
         let _guard = ValueSourceGuard::new(source, true);
         let options = toml::from_str(content)?;
@@ -156,20 +170,44 @@ impl Options {
                 ValueSource::PythonVSCodeExtension => SysPrefixPathOrigin::PythonVSCodeExtension,
             };
 
-            Some(PythonEnvironment::new(
-                python_path.absolute(project_root, system),
-                origin,
-                system,
-            )?)
+            PythonEnvironment::new(python_path.absolute(project_root, system), origin, system)
+                .map_err(anyhow::Error::from)
+                .map(Some)
         } else {
             PythonEnvironment::discover(project_root, system)
-                .context("Failed to discover local Python environment")?
+                .context("Failed to discover local Python environment")
+        };
+
+        // If in safe-mode, fallback to None if this fails instead of erroring.
+        let python_environment = match python_environment {
+            Ok(python_environment) => python_environment,
+            Err(err) => {
+                if self.safe_mode {
+                    tracing::debug!("Default settings failed to discover local Python environment");
+                    None
+                } else {
+                    return Err(err);
+                }
+            }
         };
 
         let site_packages_paths = if let Some(python_environment) = python_environment.as_ref() {
-            python_environment
+            let site_packages_paths = python_environment
                 .site_packages_paths(system)
-                .context("Failed to discover the site-packages directory")?
+                .context("Failed to discover the site-packages directory");
+            match site_packages_paths {
+                Ok(paths) => paths,
+                Err(err) => {
+                    if self.safe_mode {
+                        tracing::debug!(
+                            "Default settings failed to discover site-packages directory"
+                        );
+                        SitePackagesPaths::default()
+                    } else {
+                        return Err(err);
+                    }
+                }
+            }
         } else {
             tracing::debug!("No virtual environment found");
 
@@ -193,6 +231,7 @@ impl Options {
             .or_else(|| site_packages_paths.python_version_from_layout())
             .unwrap_or_default();
 
+        // Safe mode is handled inside this function, so we just assume this can't fail
         let search_paths = self.to_search_paths(
             project_root,
             project_name,
@@ -352,6 +391,7 @@ impl Options {
                 .map(|path| path.absolute(project_root, system)),
             site_packages_paths: site_packages_paths.into_vec(),
             real_stdlib_path,
+            safe_mode: self.safe_mode,
         };
 
         settings.to_search_paths(system, vendored)
diff --git a/crates/ty_python_semantic/src/module_resolver/resolver.rs b/crates/ty_python_semantic/src/module_resolver/resolver.rs
index 078785904921a..318ae189c4281 100644
--- a/crates/ty_python_semantic/src/module_resolver/resolver.rs
+++ b/crates/ty_python_semantic/src/module_resolver/resolver.rs
@@ -236,6 +236,7 @@ impl SearchPaths {
             custom_typeshed: typeshed,
             site_packages_paths,
             real_stdlib_path,
+            safe_mode,
         } = settings;
 
         let mut static_paths = vec![];
@@ -244,12 +245,30 @@ impl SearchPaths {
             let path = canonicalize(path, system);
             tracing::debug!("Adding extra search-path `{path}`");
 
-            static_paths.push(SearchPath::extra(system, path)?);
+            match SearchPath::extra(system, path) {
+                Ok(path) => static_paths.push(path),
+                Err(err) => {
+                    if *safe_mode {
+                        tracing::debug!("Skipping invalid extra search-path: {err}");
+                    } else {
+                        return Err(err);
+                    }
+                }
+            }
         }
 
         for src_root in src_roots {
             tracing::debug!("Adding first-party search path `{src_root}`");
-            static_paths.push(SearchPath::first_party(system, src_root.to_path_buf())?);
+            match SearchPath::first_party(system, src_root.to_path_buf()) {
+                Ok(path) => static_paths.push(path),
+                Err(err) => {
+                    if *safe_mode {
+                        tracing::debug!("Skipping invalid first-party search-path: {err}");
+                    } else {
+                        return Err(err);
+                    }
+                }
+            }
         }
 
         let (typeshed_versions, stdlib_path) = if let Some(typeshed) = typeshed {
@@ -258,18 +277,31 @@ impl SearchPaths {
 
             let versions_path = typeshed.join("stdlib/VERSIONS");
 
-            let versions_content = system.read_to_string(&versions_path).map_err(|error| {
-                SearchPathValidationError::FailedToReadVersionsFile {
-                    path: versions_path,
-                    error,
+            let results = system
+                .read_to_string(&versions_path)
+                .map_err(
+                    |error| SearchPathValidationError::FailedToReadVersionsFile {
+                        path: versions_path,
+                        error,
+                    },
+                )
+                .and_then(|versions_content| Ok(versions_content.parse()?))
+                .and_then(|parsed| Ok((parsed, SearchPath::custom_stdlib(system, &typeshed)?)));
+
+            match results {
+                Ok(results) => results,
+                Err(err) => {
+                    if settings.safe_mode {
+                        tracing::debug!("Skipping custom-stdlib search-path: {err}");
+                        (
+                            vendored_typeshed_versions(vendored),
+                            SearchPath::vendored_stdlib(),
+                        )
+                    } else {
+                        return Err(err);
+                    }
                 }
-            })?;
-
-            let parsed: TypeshedVersions = versions_content.parse()?;
-
-            let search_path = SearchPath::custom_stdlib(system, &typeshed)?;
-
-            (parsed, search_path)
+            }
         } else {
             tracing::debug!("Using vendored stdlib");
             (
@@ -279,7 +311,17 @@ impl SearchPaths {
         };
 
         let real_stdlib_path = if let Some(path) = real_stdlib_path {
-            Some(SearchPath::real_stdlib(system, path.clone())?)
+            match SearchPath::real_stdlib(system, path.clone()) {
+                Ok(path) => Some(path),
+                Err(err) => {
+                    if *safe_mode {
+                        tracing::debug!("Skipping invalid real-stdlib search-path: {err}");
+                        None
+                    } else {
+                        return Err(err);
+                    }
+                }
+            }
         } else {
             None
         };
@@ -288,7 +330,16 @@ impl SearchPaths {
 
         for path in site_packages_paths {
             tracing::debug!("Adding site-packages search path `{path}`");
-            site_packages.push(SearchPath::site_packages(system, path.clone())?);
+            match SearchPath::site_packages(system, path.clone()) {
+                Ok(path) => site_packages.push(path),
+                Err(err) => {
+                    if settings.safe_mode {
+                        tracing::debug!("Skipping invalid real-stdlib search-path: {err}");
+                    } else {
+                        return Err(err);
+                    }
+                }
+            }
         }
 
         // TODO vendor typeshed's third-party stubs as well as the stdlib and
diff --git a/crates/ty_python_semantic/src/program.rs b/crates/ty_python_semantic/src/program.rs
index 8f06527951e1f..f7d1cc5c2251a 100644
--- a/crates/ty_python_semantic/src/program.rs
+++ b/crates/ty_python_semantic/src/program.rs
@@ -184,6 +184,12 @@ pub struct SearchPathSettings {
     /// We should ideally only ever use this for things like goto-definition,
     /// where typeshed isn't the right answer.
     pub real_stdlib_path: Option<SystemPathBuf>,
+
+    /// Settings Failure Is Not An Error.
+    ///
+    /// This is used by the default database, which we are incentivized to make infallible,
+    /// while still trying to "do our best" to set things up properly where we can.
+    pub safe_mode: bool,
 }
 
 impl SearchPathSettings {
@@ -201,6 +207,7 @@ impl SearchPathSettings {
             custom_typeshed: None,
             site_packages_paths: vec![],
             real_stdlib_path: None,
+            safe_mode: false,
         }
     }
 
diff --git a/crates/ty_server/src/session.rs b/crates/ty_server/src/session.rs
index 24ad0ef55e5c6..6e40cdbd8727c 100644
--- a/crates/ty_server/src/session.rs
+++ b/crates/ty_server/src/session.rs
@@ -540,7 +540,7 @@ impl Session {
                     ));
 
                     let db_with_default_settings =
-                        ProjectMetadata::from_options(Options::default(), root, None)
+                        ProjectMetadata::from_options(Options::safe(), root, None)
                             .context("Failed to convert default options to metadata")
                             .and_then(|metadata| ProjectDatabase::new(metadata, system))
                             .expect("Default configuration to be valid");
diff --git a/crates/ty_test/src/lib.rs b/crates/ty_test/src/lib.rs
index f66eaaf26a48d..9617e1fea3de8 100644
--- a/crates/ty_test/src/lib.rs
+++ b/crates/ty_test/src/lib.rs
@@ -307,6 +307,7 @@ fn run_test(
             custom_typeshed: custom_typeshed_path.map(SystemPath::to_path_buf),
             site_packages_paths,
             real_stdlib_path: None,
+            safe_mode: false,
         }
         .to_search_paths(db.system(), db.vendored())
         .expect("Failed to resolve search path settings"),