diff --git a/crates/typst-layout/src/lists.rs b/crates/typst-layout/src/lists.rs
index 63127474b..f8d910abf 100644
--- a/crates/typst-layout/src/lists.rs
+++ b/crates/typst-layout/src/lists.rs
@@ -6,7 +6,7 @@ use typst_library::foundations::{Content, Context, Depth, Packed, StyleChain};
 use typst_library::introspection::Locator;
 use typst_library::layout::grid::resolve::{Cell, CellGrid};
 use typst_library::layout::{Axes, Fragment, HAlignment, Regions, Sizing, VAlignment};
-use typst_library::model::{EnumElem, ListElem, Numbering, ParElem};
+use typst_library::model::{EnumElem, ListElem, Numbering, ParElem, ParbreakElem};
 use typst_library::text::TextElem;
 
 use crate::grid::GridLayouter;
@@ -22,8 +22,9 @@ pub fn layout_list(
 ) -> SourceResult<Fragment> {
     let indent = elem.indent(styles);
     let body_indent = elem.body_indent(styles);
+    let tight = elem.tight(styles);
     let gutter = elem.spacing(styles).unwrap_or_else(|| {
-        if elem.tight(styles) {
+        if tight {
             ParElem::leading_in(styles).into()
         } else {
             ParElem::spacing_in(styles).into()
@@ -41,11 +42,17 @@ pub fn layout_list(
     let mut locator = locator.split();
 
     for item in &elem.children {
+        // Text in wide lists shall always turn into paragraphs.
+        let mut body = item.body.clone();
+        if !tight {
+            body += ParbreakElem::shared();
+        }
+
         cells.push(Cell::new(Content::empty(), locator.next(&())));
         cells.push(Cell::new(marker.clone(), locator.next(&marker.span())));
         cells.push(Cell::new(Content::empty(), locator.next(&())));
         cells.push(Cell::new(
-            item.body.clone().styled(ListElem::set_depth(Depth(1))),
+            body.styled(ListElem::set_depth(Depth(1))),
             locator.next(&item.body.span()),
         ));
     }
@@ -78,8 +85,9 @@ pub fn layout_enum(
     let reversed = elem.reversed(styles);
     let indent = elem.indent(styles);
     let body_indent = elem.body_indent(styles);
+    let tight = elem.tight(styles);
     let gutter = elem.spacing(styles).unwrap_or_else(|| {
-        if elem.tight(styles) {
+        if tight {
             ParElem::leading_in(styles).into()
         } else {
             ParElem::spacing_in(styles).into()
@@ -124,11 +132,17 @@ pub fn layout_enum(
         let resolved =
             resolved.aligned(number_align).styled(TextElem::set_overhang(false));
 
+        // Text in wide enums shall always turn into paragraphs.
+        let mut body = item.body.clone();
+        if !tight {
+            body += ParbreakElem::shared();
+        }
+
         cells.push(Cell::new(Content::empty(), locator.next(&())));
         cells.push(Cell::new(resolved, locator.next(&())));
         cells.push(Cell::new(Content::empty(), locator.next(&())));
         cells.push(Cell::new(
-            item.body.clone().styled(EnumElem::set_parents(smallvec![number])),
+            body.styled(EnumElem::set_parents(smallvec![number])),
             locator.next(&item.body.span()),
         ));
         number =
diff --git a/crates/typst-library/src/model/enum.rs b/crates/typst-library/src/model/enum.rs
index 4dc834ab7..a4126e72c 100644
--- a/crates/typst-library/src/model/enum.rs
+++ b/crates/typst-library/src/model/enum.rs
@@ -11,7 +11,9 @@ use crate::foundations::{
 };
 use crate::html::{attr, tag, HtmlElem};
 use crate::layout::{Alignment, BlockElem, Em, HAlignment, Length, VAlignment, VElem};
-use crate::model::{ListItemLike, ListLike, Numbering, NumberingPattern, ParElem};
+use crate::model::{
+    ListItemLike, ListLike, Numbering, NumberingPattern, ParElem, ParbreakElem,
+};
 
 /// A numbered list.
 ///
@@ -226,6 +228,8 @@ impl EnumElem {
 
 impl Show for Packed<EnumElem> {
     fn show(&self, engine: &mut Engine, styles: StyleChain) -> SourceResult<Content> {
+        let tight = self.tight(styles);
+
         if TargetElem::target_in(styles).is_html() {
             let mut elem = HtmlElem::new(tag::ol);
             if self.reversed(styles) {
@@ -239,7 +243,12 @@ impl Show for Packed<EnumElem> {
                 if let Some(nr) = item.number(styles) {
                     li = li.with_attr(attr::value, eco_format!("{nr}"));
                 }
-                li.with_body(Some(item.body.clone())).pack().spanned(item.span())
+                // Text in wide enums shall always turn into paragraphs.
+                let mut body = item.body.clone();
+                if !tight {
+                    body += ParbreakElem::shared();
+                }
+                li.with_body(Some(body)).pack().spanned(item.span())
             }));
             return Ok(elem.with_body(Some(body)).pack().spanned(self.span()));
         }
@@ -249,7 +258,7 @@ impl Show for Packed<EnumElem> {
                 .pack()
                 .spanned(self.span());
 
-        if self.tight(styles) {
+        if tight {
             let leading = ParElem::leading_in(styles);
             let spacing =
                 VElem::new(leading.into()).with_weak(true).with_attach(true).pack();
diff --git a/crates/typst-library/src/model/list.rs b/crates/typst-library/src/model/list.rs
index 1e369d541..d93ec9172 100644
--- a/crates/typst-library/src/model/list.rs
+++ b/crates/typst-library/src/model/list.rs
@@ -8,7 +8,7 @@ use crate::foundations::{
 };
 use crate::html::{tag, HtmlElem};
 use crate::layout::{BlockElem, Em, Length, VElem};
-use crate::model::ParElem;
+use crate::model::{ParElem, ParbreakElem};
 use crate::text::TextElem;
 
 /// A bullet list.
@@ -141,11 +141,18 @@ impl ListElem {
 
 impl Show for Packed<ListElem> {
     fn show(&self, engine: &mut Engine, styles: StyleChain) -> SourceResult<Content> {
+        let tight = self.tight(styles);
+
         if TargetElem::target_in(styles).is_html() {
             return Ok(HtmlElem::new(tag::ul)
                 .with_body(Some(Content::sequence(self.children.iter().map(|item| {
+                    // Text in wide lists shall always turn into paragraphs.
+                    let mut body = item.body.clone();
+                    if !tight {
+                        body += ParbreakElem::shared();
+                    }
                     HtmlElem::new(tag::li)
-                        .with_body(Some(item.body.clone()))
+                        .with_body(Some(body))
                         .pack()
                         .spanned(item.span())
                 }))))
@@ -158,7 +165,7 @@ impl Show for Packed<ListElem> {
                 .pack()
                 .spanned(self.span());
 
-        if self.tight(styles) {
+        if tight {
             let leading = ParElem::leading_in(styles);
             let spacing =
                 VElem::new(leading.into()).with_weak(true).with_attach(true).pack();
diff --git a/crates/typst-library/src/model/terms.rs b/crates/typst-library/src/model/terms.rs
index c91eeb17a..9a2ed6aad 100644
--- a/crates/typst-library/src/model/terms.rs
+++ b/crates/typst-library/src/model/terms.rs
@@ -8,7 +8,7 @@ use crate::foundations::{
 };
 use crate::html::{tag, HtmlElem};
 use crate::layout::{Em, HElem, Length, Sides, StackChild, StackElem, VElem};
-use crate::model::{ListItemLike, ListLike, ParElem};
+use crate::model::{ListItemLike, ListLike, ParElem, ParbreakElem};
 use crate::text::TextElem;
 
 /// A list of terms and their descriptions.
@@ -116,17 +116,25 @@ impl TermsElem {
 impl Show for Packed<TermsElem> {
     fn show(&self, _: &mut Engine, styles: StyleChain) -> SourceResult<Content> {
         let span = self.span();
+        let tight = self.tight(styles);
+
         if TargetElem::target_in(styles).is_html() {
             return Ok(HtmlElem::new(tag::dl)
                 .with_body(Some(Content::sequence(self.children.iter().flat_map(
                     |item| {
+                        // Text in wide term lists shall always turn into paragraphs.
+                        let mut description = item.description.clone();
+                        if !tight {
+                            description += ParbreakElem::shared();
+                        }
+
                         [
                             HtmlElem::new(tag::dt)
                                 .with_body(Some(item.term.clone()))
                                 .pack()
                                 .spanned(item.term.span()),
                             HtmlElem::new(tag::dd)
-                                .with_body(Some(item.description.clone()))
+                                .with_body(Some(description))
                                 .pack()
                                 .spanned(item.description.span()),
                         ]
@@ -139,7 +147,7 @@ impl Show for Packed<TermsElem> {
         let indent = self.indent(styles);
         let hanging_indent = self.hanging_indent(styles);
         let gutter = self.spacing(styles).unwrap_or_else(|| {
-            if self.tight(styles) {
+            if tight {
                 ParElem::leading_in(styles).into()
             } else {
                 ParElem::spacing_in(styles).into()
@@ -157,6 +165,12 @@ impl Show for Packed<TermsElem> {
             seq.push(child.term.clone().strong());
             seq.push((*separator).clone());
             seq.push(child.description.clone());
+
+            // Text in wide term lists shall always turn into paragraphs.
+            if !tight {
+                seq.push(ParbreakElem::shared().clone());
+            }
+
             children.push(StackChild::Block(Content::sequence(seq)));
         }
 
@@ -168,7 +182,7 @@ impl Show for Packed<TermsElem> {
             .spanned(span)
             .padded(padding);
 
-        if self.tight(styles) {
+        if tight {
             let leading = ParElem::leading_in(styles);
             let spacing = VElem::new(leading.into())
                 .with_weak(true)
diff --git a/tests/ref/enum-par.png b/tests/ref/enum-par.png
new file mode 100644
index 000000000..ca923a526
Binary files /dev/null and b/tests/ref/enum-par.png differ
diff --git a/tests/ref/html/enum-par.html b/tests/ref/html/enum-par.html
new file mode 100644
index 000000000..60d4592b7
--- /dev/null
+++ b/tests/ref/html/enum-par.html
@@ -0,0 +1,36 @@
+<!DOCTYPE html>
+<html>
+  <head>
+    <meta charset="utf-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1">
+  </head>
+  <body>
+    <div>
+      <ol>
+        <li>Hello</li>
+        <li>World</li>
+      </ol>
+    </div>
+    <div>
+      <ol>
+        <li>
+          <p>Hello</p>
+          <p>From</p>
+        </li>
+        <li>World</li>
+      </ol>
+    </div>
+    <div>
+      <ol>
+        <li>
+          <p>Hello</p>
+          <p>From</p>
+          <p>The</p>
+        </li>
+        <li>
+          <p>World</p>
+        </li>
+      </ol>
+    </div>
+  </body>
+</html>
diff --git a/tests/ref/html/list-par.html b/tests/ref/html/list-par.html
new file mode 100644
index 000000000..7c747ff44
--- /dev/null
+++ b/tests/ref/html/list-par.html
@@ -0,0 +1,36 @@
+<!DOCTYPE html>
+<html>
+  <head>
+    <meta charset="utf-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1">
+  </head>
+  <body>
+    <div>
+      <ul>
+        <li>Hello</li>
+        <li>World</li>
+      </ul>
+    </div>
+    <div>
+      <ul>
+        <li>
+          <p>Hello</p>
+          <p>From</p>
+        </li>
+        <li>World</li>
+      </ul>
+    </div>
+    <div>
+      <ul>
+        <li>
+          <p>Hello</p>
+          <p>From</p>
+          <p>The</p>
+        </li>
+        <li>
+          <p>World</p>
+        </li>
+      </ul>
+    </div>
+  </body>
+</html>
diff --git a/tests/ref/html/terms-par.html b/tests/ref/html/terms-par.html
new file mode 100644
index 000000000..78bc5df16
--- /dev/null
+++ b/tests/ref/html/terms-par.html
@@ -0,0 +1,42 @@
+<!DOCTYPE html>
+<html>
+  <head>
+    <meta charset="utf-8">
+    <meta name="viewport" content="width=device-width, initial-scale=1">
+  </head>
+  <body>
+    <div>
+      <dl>
+        <dt>Hello</dt>
+        <dd>A</dd>
+        <dt>World</dt>
+        <dd>B</dd>
+      </dl>
+    </div>
+    <div>
+      <dl>
+        <dt>Hello</dt>
+        <dd>
+          <p>A</p>
+          <p>From</p>
+        </dd>
+        <dt>World</dt>
+        <dd>B</dd>
+      </dl>
+    </div>
+    <div>
+      <dl>
+        <dt>Hello</dt>
+        <dd>
+          <p>A</p>
+          <p>From</p>
+          <p>The</p>
+        </dd>
+        <dt>World</dt>
+        <dd>
+          <p>B</p>
+        </dd>
+      </dl>
+    </div>
+  </body>
+</html>
diff --git a/tests/ref/issue-5503-enum-in-align.png b/tests/ref/issue-5503-enum-in-align.png
new file mode 100644
index 000000000..4857e731b
Binary files /dev/null and b/tests/ref/issue-5503-enum-in-align.png differ
diff --git a/tests/ref/issue-5503-enum-interrupted-by-par-align.png b/tests/ref/issue-5503-enum-interrupted-by-par-align.png
deleted file mode 100644
index 9cc942b4c..000000000
Binary files a/tests/ref/issue-5503-enum-interrupted-by-par-align.png and /dev/null differ
diff --git a/tests/ref/issue-5503-list-interrupted-by-par-align.png b/tests/ref/issue-5503-list-in-align.png
similarity index 100%
rename from tests/ref/issue-5503-list-interrupted-by-par-align.png
rename to tests/ref/issue-5503-list-in-align.png
diff --git a/tests/ref/issue-5503-terms-interrupted-by-par-align.png b/tests/ref/issue-5503-terms-in-align.png
similarity index 100%
rename from tests/ref/issue-5503-terms-interrupted-by-par-align.png
rename to tests/ref/issue-5503-terms-in-align.png
diff --git a/tests/ref/list-par.png b/tests/ref/list-par.png
new file mode 100644
index 000000000..5f0003d17
Binary files /dev/null and b/tests/ref/list-par.png differ
diff --git a/tests/ref/terms-par.png b/tests/ref/terms-par.png
new file mode 100644
index 000000000..910b5e5da
Binary files /dev/null and b/tests/ref/terms-par.png differ
diff --git a/tests/suite/model/enum.typ b/tests/suite/model/enum.typ
index 288392d45..7176b04e2 100644
--- a/tests/suite/model/enum.typ
+++ b/tests/suite/model/enum.typ
@@ -183,22 +183,44 @@ a + 0.
 #set enum(number-align: horizon)
 #set enum(number-align: bottom)
 
+--- enum-par render html ---
+// Check whether the contents of enum items become paragraphs.
+#show par: it => if target() != "html" { highlight(it) } else { it }
+
+// No paragraphs.
+#block[
+  + Hello
+  + World
+]
+
+#block[
+  + Hello // Paragraphs
+
+    From
+  + World // No paragraph because it's a tight enum
+]
+
+#block[
+  + Hello // Paragraphs
+
+    From
+
+    The
+
+  + World // Paragraph because it's a wide enum
+]
+
 --- issue-2530-enum-item-panic ---
 // Enum item (pre-emptive)
 #enum.item(none)[Hello]
 #enum.item(17)[Hello]
 
---- issue-5503-enum-interrupted-by-par-align ---
-// `align` is block-level and should interrupt an enum
-// but not a `par`
+--- issue-5503-enum-in-align ---
+// `align` is block-level and should interrupt an enum.
 + a
 + b
-#par(leading: 5em)[+ par]
+#align(right)[+ c]
 + d
-#par[+ par]
-+ f
-#align(right)[+ align]
-+ h
 
 --- issue-5719-enum-nested ---
 // Enums can be immediately nested.
diff --git a/tests/suite/model/list.typ b/tests/suite/model/list.typ
index 96ddf3c18..9bed930bb 100644
--- a/tests/suite/model/list.typ
+++ b/tests/suite/model/list.typ
@@ -238,6 +238,33 @@ World
 #text(red)[- World]
 #text(green)[- What up?]
 
+--- list-par render html ---
+// Check whether the contents of list items become paragraphs.
+#show par: it => if target() != "html" { highlight(it) } else { it }
+
+#block[
+  // No paragraphs.
+  - Hello
+  - World
+]
+
+#block[
+  - Hello // Paragraphs
+
+    From
+  - World // No paragraph because it's a tight list.
+]
+
+#block[
+  - Hello // Paragraphs either way
+
+    From
+
+    The
+
+  - World // Paragraph because it's a wide list.
+]
+
 --- issue-2530-list-item-panic ---
 // List item (pre-emptive)
 #list.item[Hello]
@@ -262,18 +289,11 @@ World
   part($ x $ + parbreak() + parbreak() + list[A])
 }
 
---- issue-5503-list-interrupted-by-par-align ---
-// `align` is block-level and should interrupt a list
-// but not a `par`
+--- issue-5503-list-in-align ---
+// `align` is block-level and should interrupt a list.
 #show list: [List]
 - a
 - b
-#par(leading: 5em)[- c]
-- d
-- e
-#par[- f]
-- g
-- h
 #align(right)[- i]
 - j
 
diff --git a/tests/suite/model/terms.typ b/tests/suite/model/terms.typ
index 23ac6e513..103a8033e 100644
--- a/tests/suite/model/terms.typ
+++ b/tests/suite/model/terms.typ
@@ -59,6 +59,34 @@ Not in list
 // Error: 8 expected colon
 / Hello
 
+--- terms-par render html ---
+// Check whether the contents of term list items become paragraphs.
+#show par: it => if target() != "html" { highlight(it) } else { it }
+
+// No paragraphs.
+#block[
+  / Hello: A
+  / World: B
+]
+
+#block[
+  / Hello: A // Paragraphs
+
+    From
+  / World: B // No paragraphs because it's a tight term list.
+]
+
+#block[
+  / Hello: A // Paragraphs
+
+    From
+
+    The
+
+  / World: B // Paragraph because it's a wide term list.
+]
+
+
 --- issue-1050-terms-indent ---
 #set page(width: 110pt)
 #set par(first-line-indent: 0.5cm)
@@ -76,18 +104,10 @@ Not in list
 // Term item (pre-emptive)
 #terms.item[Hello][World!]
 
---- issue-5503-terms-interrupted-by-par-align ---
-// `align` is block-level and should interrupt a `terms`
-// but not a `par`
+--- issue-5503-terms-in-align ---
+// `align` is block-level and should interrupt a `terms`.
 #show terms: [Terms]
 / a: a
-/ b: b
-#par(leading: 5em)[/ c: c]
-/ d: d
-/ e: e
-#par[/ f: f]
-/ g: g
-/ h: h
 #align(right)[/ i: i]
 / j: j