diff --git a/src/geom/length.rs b/src/geom/length.rs
index ecfe56163..951cef4f6 100644
--- a/src/geom/length.rs
+++ b/src/geom/length.rs
@@ -108,6 +108,11 @@ impl Length {
         self.raw + 1e-6 >= other.raw
     }
 
+    /// Compares two lengths for whether they are approximately equal.
+    pub fn approx_eq(self, other: Self) -> bool {
+        self == other || (self - other).to_raw().abs() < 1e-6
+    }
+
     /// Whether the length is zero.
     pub fn is_zero(self) -> bool {
         self.raw == 0.0
diff --git a/src/layout/grid.rs b/src/layout/grid.rs
index d2976502a..33fce0642 100644
--- a/src/layout/grid.rs
+++ b/src/layout/grid.rs
@@ -56,6 +56,8 @@ struct GridLayouter<'a> {
     cross: SpecAxis,
     /// The axis of the main direction.
     main: SpecAxis,
+    /// The original expand state of the target region.
+    expand: Spec<bool>,
     /// The column tracks including gutter tracks.
     cols: Vec<TrackSizing>,
     /// The row tracks including gutter tracks.
@@ -135,7 +137,8 @@ impl<'a> GridLayouter<'a> {
         let full = regions.current.get(main);
         let rcols = vec![Length::zero(); cols.len()];
 
-        // We use the regions only for auto row measurement.
+        // We use the regions only for auto row measurement and constraints.
+        let expand = regions.expand;
         regions.expand = Gen::new(true, false).to_spec(main);
 
         Self {
@@ -144,8 +147,9 @@ impl<'a> GridLayouter<'a> {
             cols,
             rows,
             children: &grid.children,
-            constraints: Constraints::new(regions.expand),
+            constraints: Constraints::new(expand),
             regions,
+            expand,
             rcols,
             lrows: vec![],
             full,
@@ -506,7 +510,7 @@ impl<'a> GridLayouter<'a> {
         self.used.main = Length::zero();
         self.fr = Fractional::zero();
         self.finished.push(output.constrain(self.constraints));
-        self.constraints = Constraints::new(self.regions.expand);
+        self.constraints = Constraints::new(self.expand);
     }
 
     /// Get the node in the cell in column `x` and row `y`.
diff --git a/src/layout/incremental.rs b/src/layout/incremental.rs
index a5c3cea35..9eda04026 100644
--- a/src/layout/incremental.rs
+++ b/src/layout/incremental.rs
@@ -1,4 +1,5 @@
-use std::{collections::HashMap, ops::Deref};
+use std::collections::{hash_map::Entry, HashMap};
+use std::ops::Deref;
 
 use super::*;
 
@@ -6,14 +7,18 @@ use super::*;
 #[derive(Default, Debug, Clone)]
 pub struct LayoutCache {
     /// Maps from node hashes to the resulting frames and regions in which the
-    /// frames are valid.
-    pub frames: HashMap<u64, FramesEntry>,
+    /// frames are valid. The right hand side of the hash map is a vector of
+    /// results because across one or more compilations, multiple different
+    /// layouts of the same node may have been requested.
+    pub frames: HashMap<u64, Vec<FramesEntry>>,
+    /// In how many compilations this cache has been used.
+    age: usize,
 }
 
 impl LayoutCache {
     /// Create a new, empty layout cache.
     pub fn new() -> Self {
-        Self { frames: HashMap::new() }
+        Self { frames: HashMap::new(), age: 0 }
     }
 
     /// Clear the cache.
@@ -21,42 +26,143 @@ impl LayoutCache {
         self.frames.clear();
     }
 
+    /// Amount of items in the cache.
+    pub fn len(&self) -> usize {
+        self.frames.iter().map(|(_, e)| e.len()).sum()
+    }
+
     /// Retains all elements for which the closure on the level returns `true`.
     pub fn retain<F>(&mut self, mut f: F)
     where
         F: FnMut(usize) -> bool,
     {
-        self.frames.retain(|_, entry| f(entry.level));
+        for (_, entries) in self.frames.iter_mut() {
+            entries.retain(|entry| f(entry.level));
+        }
     }
 
-    /// Amount of items in the cache.
-    pub fn len(&self) -> usize {
-        self.frames.len()
+    /// Prepare the cache for the next round of compilation
+    pub fn turnaround(&mut self) {
+        self.age += 1;
+        for entry in self.frames.iter_mut().flat_map(|(_, x)| x.iter_mut()) {
+            for i in 0 .. (entry.temperature.len() - 1) {
+                entry.temperature[i + 1] = entry.temperature[i];
+            }
+            entry.temperature[0] = 0;
+            entry.age += 1;
+        }
+    }
+
+    /// The amount of levels stored in the cache.
+    pub fn levels(&self) -> usize {
+        self.frames
+            .iter()
+            .flat_map(|(_, x)| x)
+            .map(|entry| entry.level + 1)
+            .max()
+            .unwrap_or(0)
+    }
+
+    /// Fetches the appropriate entry from the cache if there is any.
+    pub fn get(
+        &mut self,
+        hash: u64,
+        regions: Regions,
+    ) -> Option<Vec<Constrained<Rc<Frame>>>> {
+        self.frames.get_mut(&hash).and_then(|frames| {
+            for frame in frames {
+                let res = frame.check(regions.clone());
+                if res.is_some() {
+                    return res;
+                }
+            }
+
+            None
+        })
+    }
+
+    /// Inserts a new frame set into the cache.
+    pub fn insert(
+        &mut self,
+        hash: u64,
+        frames: Vec<Constrained<Rc<Frame>>>,
+        level: usize,
+    ) {
+        let entry = FramesEntry::new(frames, level);
+        match self.frames.entry(hash) {
+            Entry::Occupied(o) => o.into_mut().push(entry),
+            Entry::Vacant(v) => {
+                v.insert(vec![entry]);
+            }
+        }
     }
 }
 
-#[derive(Debug, Clone)]
 /// Cached frames from past layouting.
+#[derive(Debug, Clone)]
 pub struct FramesEntry {
     /// The cached frames for a node.
     pub frames: Vec<Constrained<Rc<Frame>>>,
     /// How nested the frame was in the context is was originally appearing in.
     pub level: usize,
+    /// For how long the element already exists.
+    age: usize,
+    /// How much the element was accessed during the last five compilations, the
+    /// most recent one being the first element.
+    temperature: [usize; 5],
 }
 
 impl FramesEntry {
+    /// Construct a new instance.
+    pub fn new(frames: Vec<Constrained<Rc<Frame>>>, level: usize) -> Self {
+        Self {
+            frames,
+            level,
+            age: 1,
+            temperature: [0; 5],
+        }
+    }
+
     /// Checks if the cached [`Frame`] is valid for the given regions.
-    pub fn check(&self, mut regions: Regions) -> Option<Vec<Constrained<Rc<Frame>>>> {
+    pub fn check(&mut self, mut regions: Regions) -> Option<Vec<Constrained<Rc<Frame>>>> {
         for (i, frame) in self.frames.iter().enumerate() {
             if (i != 0 && !regions.next()) || !frame.constraints.check(&regions) {
                 return None;
             }
         }
 
+        self.temperature[0] += 1;
+
         Some(self.frames.clone())
     }
+
+    /// Get the amount of compilation cycles this item has remained in the
+    /// cache.
+    pub fn age(&self) -> usize {
+        self.age
+    }
+
+    /// Get the amount of consecutive cycles in which this item has not
+    /// been used.
+    pub fn cooldown(&self) -> usize {
+        let mut cycle = 0;
+        for &temp in &self.temperature[.. self.age] {
+            if temp > 0 {
+                return cycle;
+            }
+            cycle += 1;
+        }
+
+        cycle
+    }
+
+    /// Whether this element was used in the last compilation cycle.
+    pub fn hit(&self) -> bool {
+        self.temperature[0] != 0
+    }
 }
 
+/// Describe regions that match them.
 #[derive(Debug, Copy, Clone, PartialEq)]
 pub struct Constraints {
     /// The minimum available length in the region.
@@ -107,25 +213,40 @@ impl Constraints {
         let base = regions.base.to_spec();
         let current = regions.current.to_spec();
 
-        current.eq_by(&self.min, |x, y| y.map_or(true, |y| x >= &y))
+        current.eq_by(&self.min, |x, y| y.map_or(true, |y| x.fits(y)))
             && current.eq_by(&self.max, |x, y| y.map_or(true, |y| x < &y))
-            && current.eq_by(&self.exact, |x, y| y.map_or(true, |y| x == &y))
-            && base.eq_by(&self.base, |x, y| y.map_or(true, |y| x == &y))
+            && current.eq_by(&self.exact, |x, y| y.map_or(true, |y| x.approx_eq(y)))
+            && base.eq_by(&self.base, |x, y| y.map_or(true, |y| x.approx_eq(y)))
     }
 
-    /// Changes all constraints by adding the argument to them if they are set.
-    pub fn mutate(&mut self, size: Size) {
-        for x in &mut [self.min, self.max, self.exact, self.base] {
-            if let Some(horizontal) = x.horizontal.as_mut() {
+    /// Changes all constraints by adding the `size` to them if they are `Some`.
+    pub fn mutate(&mut self, size: Size, regions: &Regions) {
+        for spec in std::array::IntoIter::new([
+            &mut self.min,
+            &mut self.max,
+            &mut self.exact,
+            &mut self.base,
+        ]) {
+            if let Some(horizontal) = spec.horizontal.as_mut() {
                 *horizontal += size.width;
             }
-            if let Some(vertical) = x.vertical.as_mut() {
+            if let Some(vertical) = spec.vertical.as_mut() {
                 *vertical += size.height;
             }
         }
+
+        let current = regions.current.to_spec();
+        let base = regions.base.to_spec();
+
+        self.exact.horizontal.set_if_some(current.horizontal);
+        self.exact.vertical.set_if_some(current.vertical);
+        self.base.horizontal.set_if_some(base.horizontal);
+        self.base.vertical.set_if_some(base.vertical);
     }
 }
 
+/// Carries an item that only applies to certain regions and the constraints
+/// that describe these regions.
 #[derive(Debug, Copy, Clone, PartialEq)]
 pub struct Constrained<T> {
     pub item: T,
@@ -140,9 +261,19 @@ impl<T> Deref for Constrained<T> {
     }
 }
 
+/// Extends length-related options by providing convenience methods for setting
+/// minimum and maximum lengths on them, even if they are `None`.
 pub trait OptionExt {
+    // Sets `other` as the value if the Option is `None` or if it contains a
+    // value larger than `other`.
     fn set_min(&mut self, other: Length);
+
+    // Sets `other` as the value if the Option is `None` or if it contains a
+    // value smaller than `other`.
     fn set_max(&mut self, other: Length);
+
+    /// Sets `other` as the value if the Option is `Some`.
+    fn set_if_some(&mut self, other: Length);
 }
 
 impl OptionExt for Option<Length> {
@@ -159,4 +290,10 @@ impl OptionExt for Option<Length> {
             None => *self = Some(other),
         }
     }
+
+    fn set_if_some(&mut self, other: Length) {
+        if self.is_some() {
+            *self = Some(other);
+        }
+    }
 }
diff --git a/src/layout/mod.rs b/src/layout/mod.rs
index 10c30f419..dc819a164 100644
--- a/src/layout/mod.rs
+++ b/src/layout/mod.rs
@@ -102,18 +102,10 @@ impl Layout for AnyNode {
         regions: &Regions,
     ) -> Vec<Constrained<Rc<Frame>>> {
         ctx.level += 1;
-        let frames = ctx
-            .cache
-            .layout
-            .frames
-            .get(&self.hash)
-            .and_then(|x| x.check(regions.clone()))
-            .unwrap_or_else(|| {
+        let frames =
+            ctx.cache.layout.get(self.hash, regions.clone()).unwrap_or_else(|| {
                 let frames = self.node.layout(ctx, regions);
-                ctx.cache.layout.frames.insert(self.hash, FramesEntry {
-                    frames: frames.clone(),
-                    level: ctx.level - 1,
-                });
+                ctx.cache.layout.insert(self.hash, frames.clone(), ctx.level - 1);
                 frames
             });
         ctx.level -= 1;
diff --git a/src/layout/pad.rs b/src/layout/pad.rs
index 9d432e797..9461f3ff2 100644
--- a/src/layout/pad.rs
+++ b/src/layout/pad.rs
@@ -15,9 +15,11 @@ impl Layout for PadNode {
         ctx: &mut LayoutContext,
         regions: &Regions,
     ) -> Vec<Constrained<Rc<Frame>>> {
-        let mut regions = regions.map(|size| size - self.padding.resolve(size).size());
-
-        let mut frames = self.child.layout(ctx, &regions);
+        let mut regions = regions.clone();
+        let mut frames = self.child.layout(
+            ctx,
+            &regions.map(|size| size - self.padding.resolve(size).size()),
+        );
 
         for frame in &mut frames {
             let padded = solve(self.padding, frame.size);
@@ -28,7 +30,7 @@ impl Layout for PadNode {
             let prev = std::mem::take(&mut frame.item);
             new.push_frame(origin, prev);
 
-            frame.constraints.mutate(padding.size() * -1.0);
+            frame.constraints.mutate(padding.size(), &regions);
 
             if self.padding.left.is_relative() || self.padding.right.is_relative() {
                 frame.constraints.base.horizontal = Some(regions.base.width);
@@ -40,6 +42,7 @@ impl Layout for PadNode {
             regions.next();
             *Rc::make_mut(&mut frame.item) = new;
         }
+
         frames
     }
 }
diff --git a/src/layout/par.rs b/src/layout/par.rs
index 2208f9ee3..45eefe29f 100644
--- a/src/layout/par.rs
+++ b/src/layout/par.rs
@@ -190,6 +190,7 @@ impl<'a> ParLayouter<'a> {
             // line cannot be broken up further.
             if !stack.regions.current.fits(line.size) {
                 if let Some((last_line, last_end)) = last.take() {
+                    // The region must not fit this line for the result to be valid.
                     if !stack.regions.current.width.fits(line.size.width) {
                         stack.constraints.max.horizontal.set_min(line.size.width);
                     }
@@ -213,10 +214,31 @@ impl<'a> ParLayouter<'a> {
             while !stack.regions.current.height.fits(line.size.height)
                 && !stack.regions.in_full_last()
             {
-                stack.constraints.max.vertical.set_min(line.size.height);
+                // Again, the line must not fit. It would if the space taken up
+                // plus the line height would fit, therefore the constraint
+                // below.
+                stack
+                    .constraints
+                    .max
+                    .vertical
+                    .set_min(stack.size.height + line.size.height);
                 stack.finish_region(ctx);
             }
 
+            // If the line does not fit vertically, we start a new region.
+            while !stack.regions.current.height.fits(line.size.height) {
+                if stack.regions.in_full_last() {
+                    stack.overflowing = true;
+                    break;
+                }
+
+                stack
+                    .constraints
+                    .max
+                    .vertical
+                    .set_min(stack.size.height + line.size.height);
+                stack.finish_region(ctx);
+            }
             // If the line does not fit horizontally or we have a mandatory
             // line break (i.e. due to "\n"), we push the line into the
             // stack.
@@ -303,11 +325,13 @@ impl ParItem<'_> {
 /// Stacks lines on top of each other.
 struct LineStack<'a> {
     line_spacing: Length,
+    full: Size,
     regions: Regions,
     size: Size,
     lines: Vec<LineLayout<'a>>,
     finished: Vec<Constrained<Rc<Frame>>>,
     constraints: Constraints,
+    overflowing: bool,
 }
 
 impl<'a> LineStack<'a> {
@@ -316,10 +340,12 @@ impl<'a> LineStack<'a> {
         Self {
             line_spacing,
             constraints: Constraints::new(regions.expand),
+            full: regions.current,
             regions,
             size: Size::zero(),
             lines: vec![],
             finished: vec![],
+            overflowing: false,
         }
     }
 
@@ -343,6 +369,12 @@ impl<'a> LineStack<'a> {
             self.constraints.exact.horizontal = Some(self.regions.current.width);
         }
 
+        if self.overflowing {
+            self.constraints.min.vertical = None;
+            self.constraints.max.vertical = None;
+            self.constraints.exact = self.full.to_spec().map(Some);
+        }
+
         let mut output = Frame::new(self.size, self.size.height);
         let mut offset = Length::zero();
         let mut first = true;
@@ -362,6 +394,7 @@ impl<'a> LineStack<'a> {
 
         self.finished.push(output.constrain(self.constraints));
         self.regions.next();
+        self.full = self.regions.current;
         self.constraints = Constraints::new(self.regions.expand);
         self.size = Size::zero();
     }
diff --git a/src/layout/stack.rs b/src/layout/stack.rs
index 2a0b28060..fa5fd5840 100644
--- a/src/layout/stack.rs
+++ b/src/layout/stack.rs
@@ -62,6 +62,8 @@ struct StackLayouter<'a> {
     ruler: Align,
     /// The constraints for the current region.
     constraints: Constraints,
+    /// Whether the last region can fit all the remaining content.
+    overflowing: bool,
     /// Offset, alignment and frame for all children that fit into the current
     /// region. The exact positions are not known yet.
     frames: Vec<(Length, Gen<Align>, Rc<Frame>)>,
@@ -87,11 +89,12 @@ impl<'a> StackLayouter<'a> {
             stack,
             main,
             expand,
-            constraints: Constraints::new(regions.expand),
             regions,
             full,
             used: Gen::zero(),
             ruler: Align::Start,
+            constraints: Constraints::new(expand),
+            overflowing: false,
             frames: vec![],
             finished: vec![],
         }
@@ -142,10 +145,16 @@ impl<'a> StackLayouter<'a> {
         }
 
         // Find a fitting region.
-        while !self.regions.current.get(self.main).fits(size.main)
-            && !self.regions.in_full_last()
-        {
-            self.constraints.max.get_mut(self.main).set_min(size.main);
+        while !self.regions.current.get(self.main).fits(size.main) {
+            if self.regions.in_full_last() {
+                self.overflowing = true;
+                break;
+            }
+
+            self.constraints
+                .max
+                .get_mut(self.main)
+                .set_min(self.used.main + size.main);
             self.finish_region();
         }
 
@@ -188,7 +197,9 @@ impl<'a> StackLayouter<'a> {
 
         // Make sure the stack's size satisfies the aspect ratio.
         if let Some(aspect) = self.stack.aspect {
-            self.constraints.exact = self.regions.current.to_spec().map(Some);
+            self.constraints.exact = self.full.to_spec().map(Some);
+            self.constraints.min = Spec::splat(None);
+            self.constraints.max = Spec::splat(None);
             let width = size
                 .width
                 .max(aspect.into_inner() * size.height)
@@ -198,6 +209,12 @@ impl<'a> StackLayouter<'a> {
             size = Size::new(width, width / aspect.into_inner());
         }
 
+        if self.overflowing {
+            self.constraints.min.vertical = None;
+            self.constraints.max.vertical = None;
+            self.constraints.exact = self.full.to_spec().map(Some);
+        }
+
         let mut output = Frame::new(size, size.height);
         let mut first = true;
 
@@ -244,6 +261,6 @@ impl<'a> StackLayouter<'a> {
         self.used = Gen::zero();
         self.ruler = Align::Start;
         self.finished.push(output.constrain(self.constraints));
-        self.constraints = Constraints::new(self.regions.expand);
+        self.constraints = Constraints::new(expand);
     }
 }
diff --git a/tests/ref/layout/stack.png b/tests/ref/layout/stack.png
index 684905f73..2f190c4d3 100644
Binary files a/tests/ref/layout/stack.png and b/tests/ref/layout/stack.png differ
diff --git a/tests/typ/layout/stack.typ b/tests/typ/layout/stack.typ
index 006a1412e..89e587c73 100644
--- a/tests/typ/layout/stack.typ
+++ b/tests/typ/layout/stack.typ
@@ -7,3 +7,12 @@
     rect(3cm, forest),
     rect(1cm, conifer),
 )
+
+---
+// Test overflowing stack.
+
+#let rect(width, color) = rect(width: 1cm, height: 0.4cm, fill: color)
+#box(height: 0.5cm, stack(
+    rect(3cm, forest),
+    rect(1cm, conifer),
+))
diff --git a/tests/typeset.rs b/tests/typeset.rs
index c5f31e61f..31da3ce0f 100644
--- a/tests/typeset.rs
+++ b/tests/typeset.rs
@@ -16,13 +16,13 @@ use walkdir::WalkDir;
 use typst::cache::Cache;
 use typst::color;
 use typst::diag::{Diag, DiagSet, Level};
-use typst::eval::{EvalContext, FuncArgs, FuncValue, Scope, Value};
-use typst::exec::State;
+use typst::eval::{eval, EvalContext, FuncArgs, FuncValue, Scope, Value};
+use typst::exec::{exec, State};
 use typst::geom::{self, Length, Point, Sides, Size};
 use typst::image::ImageId;
-use typst::layout::{Element, Fill, Frame, Shape, Text};
+use typst::layout::{layout, Element, Fill, Frame, Shape, Text};
 use typst::loading::FsLoader;
-use typst::parse::{LineMap, Scanner};
+use typst::parse::{parse, LineMap, Scanner};
 use typst::syntax::{Location, Pos};
 
 const TYP_DIR: &str = "./typ";
@@ -224,14 +224,20 @@ fn test_part(
     state.page.size = Size::new(Length::pt(120.0), Length::inf());
     state.page.margins = Sides::splat(Some(Length::pt(10.0).into()));
 
-    // Clear cache between tests (for now).
-    cache.layout.clear();
+    let parsed = parse(src);
+    let evaluated = eval(
+        loader,
+        cache,
+        Some(src_path),
+        Rc::new(parsed.output),
+        &scope,
+    );
+    let executed = exec(&evaluated.output.template, state.clone());
+    let mut layouted = layout(loader, cache, &executed.output);
 
-    let mut pass = typst::typeset(loader, cache, Some(src_path), &src, &scope, state);
-
-    if !compare_ref {
-        pass.output.clear();
-    }
+    let mut diags = parsed.diags;
+    diags.extend(evaluated.diags);
+    diags.extend(executed.diags);
 
     let mut ok = true;
 
@@ -247,11 +253,11 @@ fn test_part(
         ok = false;
     }
 
-    if pass.diags != ref_diags {
+    if diags != ref_diags {
         println!("  Subtest {} does not match expected diagnostics. ❌", i);
         ok = false;
 
-        for diag in &pass.diags {
+        for diag in &diags {
             if !ref_diags.contains(diag) {
                 print!("    Not annotated | ");
                 print_diag(diag, &map, lines);
@@ -259,14 +265,58 @@ fn test_part(
         }
 
         for diag in &ref_diags {
-            if !pass.diags.contains(diag) {
+            if !diags.contains(diag) {
                 print!("    Not emitted   | ");
                 print_diag(diag, &map, lines);
             }
         }
     }
 
-    (ok, compare_ref, pass.output)
+    let reference_cache = cache.layout.clone();
+    for level in 0 .. reference_cache.levels() {
+        cache.layout = reference_cache.clone();
+        cache.layout.retain(|x| x == level);
+        if cache.layout.frames.is_empty() {
+            continue;
+        }
+
+        cache.layout.turnaround();
+
+        let cached_result = layout(loader, cache, &executed.output);
+
+        let misses = cache
+            .layout
+            .frames
+            .iter()
+            .flat_map(|(_, e)| e)
+            .filter(|e| e.level == level && !e.hit() && e.age() == 2)
+            .count();
+
+        if misses > 0 {
+            ok = false;
+            println!(
+                "    Recompilation had {} cache misses on level {} (Subtest {}) ❌",
+                misses, level, i
+            );
+        }
+
+        if cached_result != layouted {
+            ok = false;
+            println!(
+                "    Recompilation of subtest {} differs from clean pass ❌",
+                i
+            );
+        }
+    }
+
+    cache.layout = reference_cache;
+    cache.layout.turnaround();
+
+    if !compare_ref {
+        layouted.clear();
+    }
+
+    (ok, compare_ref, layouted)
 }
 
 fn parse_metadata(src: &str, map: &LineMap) -> (Option<bool>, DiagSet) {