diff --git a/src/explain.rs b/src/explain.rs
index 33632ef..4d31d79 100644
--- a/src/explain.rs
+++ b/src/explain.rs
@@ -10,6 +10,7 @@ pub trait Explain: Sealed {
 }
 
 impl<T, E> Sealed for Result<T, E> where Result<T, E>: IntoResultHow {}
+impl<T> Sealed for Option<T> where Option<T>: IntoResultHow {}
 
 impl<T, E> Explain for Result<T, E>
 where
@@ -19,6 +20,18 @@ where
 
     #[inline(always)]
     fn context(self, context: impl IntoContext) -> Self::Output {
-        self.into_result_how().map_err(|e| e.context(context))
+        self.into_result_how().map_err(#[inline(never)] move |e| e.context(context))
+    }
+}
+
+impl<T> Explain for Option<T>
+where
+    Option<T>: IntoResultHow,
+{
+    type Output = Result<<Self as IntoResultHow>::T, How>;
+
+    #[inline(always)]
+    fn context(self, context: impl IntoContext) -> Self::Output {
+        self.into_result_how().map_err(#[inline(never)] move |e| e.context(context))
     }
 }
diff --git a/src/how.rs b/src/how.rs
new file mode 100644
index 0000000..6dbbd4d
--- /dev/null
+++ b/src/how.rs
@@ -0,0 +1,101 @@
+use crate::*;
+
+use crate::report::report_write;
+
+/// Does not implement [`std::error::Error`] to allow a [`From`] implementation for all other error types.
+pub struct How(Box<HowInner>);
+
+struct HowInner {
+    /// When true, the error will cause branchers to abort.
+    classified: bool,
+    #[cfg(feature = "backtrace")]
+    backtrace: std::backtrace::Backtrace,
+    // TODO: consider storing this vec inline (sharing the allocation with rest of the struct.
+    // Probably move after `backtrace`)
+    context: Vec<Context>,
+}
+
+impl std::fmt::Debug for How {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        let mut b = f.debug_struct(std::any::type_name::<Self>());
+        let b = b
+            .field("classified", &self.0.classified)
+            .field("context", &(&self.0.context));
+        #[cfg(feature = "backtrace")]
+        let b = b.field("backtrace", &self.0.backtrace);
+        b.finish()
+    }
+}
+
+impl How {
+    #[must_use]
+    #[inline(never)]
+    pub fn new(context: impl IntoContext) -> Self {
+        Self(Box::new(HowInner {
+            classified: false,
+            context: {
+                let mut vec = Vec::with_capacity(4);
+                vec[0] = context.into_context();
+                vec
+            },
+            #[cfg(feature = "backtrace")]
+            backtrace: std::backtrace::Backtrace::capture(),
+        }))
+    }
+
+    #[must_use]
+    pub fn clone_without_backtrace(&self) -> Self {
+        Self(Box::new(HowInner {
+            classified: self.0.classified,
+            context: self.0.context.clone(),
+            #[cfg(feature = "backtrace")]
+            backtrace: std::backtrace::Backtrace::disabled(),
+        }))
+    }
+
+    #[inline]
+    #[must_use]
+    pub fn classified(mut self) -> Self {
+        self.0.classified = true;
+        self
+    }
+
+    #[inline]
+    #[must_use]
+    pub const fn is_classified(&self) -> bool {
+        self.0.classified
+    }
+}
+
+impl explain::Sealed for How {}
+
+impl Explain for How {
+    type Output = Self;
+
+    #[inline(always)]
+    #[must_use]
+    fn context(mut self, context: impl IntoContext) -> Self {
+        self.0.context.push(context.into_context());
+        self
+    }
+}
+
+impl std::fmt::Display for How {
+    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
+        let mut opts = ReportOpts::default();
+        let mut ctxs = self.0.context.iter().rev();
+        let ctx = ctxs.next().expect("`How` created with no context.");
+        report_write!(f, &opts, "{ctx}")?;
+        for ctx in ctxs {
+            report_write!(f, &opts, "\n└ ")?;
+            report_write!(f, &opts.indent().next(), "{ctx}")?;
+            opts = opts.indent();
+        }
+        #[cfg(feature = "backtrace")]
+        {
+            opts = opts.indent();
+            report_write!(f, &opts, "\n{}", self.0.backtrace)?;
+        }
+        Ok(())
+    }
+}
diff --git a/src/into.rs b/src/into.rs
index d10e564..e01f6d5 100644
--- a/src/into.rs
+++ b/src/into.rs
@@ -19,9 +19,13 @@ where
 {
     type T = T;
 
-    #[inline]
+    #[inline(always)]
     fn into_result_how(self) -> Result<Self::T, How> {
-        self.map_err(|e| How::new(e.to_string()))
+        #[inline(never)]
+        fn into<E: std::error::Error>(e: E) -> How {
+            How::new(e.to_string())
+        }
+        self.map_err(into)
     }
 }
 
@@ -33,3 +37,16 @@ impl<T> IntoResultHow for Result<T, How> {
         self
     }
 }
+
+impl<T> IntoResultHow for Option<T> {
+    type T = T;
+
+    #[inline(always)]
+    fn into_result_how(self) -> Result<Self::T, How> {
+        #[inline(never)]
+        fn into() -> How {
+            How::new("None")
+        }
+        self.ok_or_else(into)
+    }
+}
diff --git a/src/lib.rs b/src/lib.rs
index 3ec808f..25a524d 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -8,7 +8,6 @@ mod context;
 pub use context::{Context, IntoContext};
 
 mod report;
-use report::report_write;
 pub use report::{Report, ReportOpts};
 
 mod into;
@@ -22,101 +21,7 @@ mod termination;
 #[cfg(feature = "termination")]
 pub use termination::TerminationResult;
 
+mod how;
+pub use how::How;
+
 pub type Result<T, E = How> = std::result::Result<T, E>;
-
-/// Does not implement [`std::error::Error`] to allow a [`From`] implementation for all other error types.
-pub struct How(Box<HowInner>);
-
-struct HowInner {
-    /// When true, the error will cause branchers to abort.
-    classified: bool,
-    // TODO: consider storing this vec inline (sharing the allocation with rest of the struct.
-    // Probably move after `backtrace`)
-    context: Vec<Context>,
-    #[cfg(feature = "backtrace")]
-    backtrace: std::backtrace::Backtrace,
-}
-
-impl std::fmt::Debug for How {
-    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-        let mut b = f.debug_struct(std::any::type_name::<Self>());
-        let b = b
-            .field("classified", &self.0.classified)
-            .field("context", &self.0.context);
-        #[cfg(feature = "backtrace")]
-        let b = b.field("backtrace", &self.0.backtrace);
-        b.finish()
-    }
-}
-
-impl How {
-    #[must_use]
-    pub fn new(context: impl IntoContext) -> Self {
-        Self(Box::new(HowInner {
-            classified: false,
-            context: {
-                let mut vec = Vec::with_capacity(2);
-                vec.push(context.into_context());
-                vec
-            },
-            #[cfg(feature = "backtrace")]
-            backtrace: std::backtrace::Backtrace::capture(),
-        }))
-    }
-
-    #[must_use]
-    pub fn clone_without_backtrace(&self) -> Self {
-        Self(Box::new(HowInner {
-            classified: self.0.classified,
-            context: self.0.context.clone(),
-            #[cfg(feature = "backtrace")]
-            backtrace: std::backtrace::Backtrace::disabled(),
-        }))
-    }
-
-    #[inline]
-    #[must_use]
-    pub fn classified(mut self) -> Self {
-        self.0.classified = true;
-        self
-    }
-
-    #[inline]
-    #[must_use]
-    pub const fn is_classified(&self) -> bool {
-        self.0.classified
-    }
-}
-
-impl explain::Sealed for How {}
-
-impl Explain for How {
-    type Output = Self;
-
-    #[inline]
-    #[must_use]
-    fn context(mut self, context: impl IntoContext) -> Self {
-        self.0.context.push(context.into_context());
-        self
-    }
-}
-
-impl std::fmt::Display for How {
-    fn fmt(&self, f: &mut std::fmt::Formatter<'_>) -> std::fmt::Result {
-        let mut opts = ReportOpts::default();
-        let mut ctxs = self.0.context.iter().rev();
-        let ctx = ctxs.next().expect("`How` created with no context.");
-        report_write!(f, &opts, "{ctx}")?;
-        for ctx in ctxs {
-            report_write!(f, &opts, "\n└ ")?;
-            report_write!(f, &opts.indent().next(), "{ctx}")?;
-            opts = opts.indent();
-        }
-        #[cfg(feature = "backtrace")]
-        {
-            opts = opts.indent();
-            report_write!(f, &opts, "\n{}", self.0.backtrace)?;
-        }
-        Ok(())
-    }
-}