diff --git a/.github/workflows/contrib.yml b/.github/workflows/contrib.yml
index 1872ae11c..ee1529194 100644
--- a/.github/workflows/contrib.yml
+++ b/.github/workflows/contrib.yml
@@ -19,7 +19,7 @@ jobs:
     - name: Install mdbook
       run: |
         mkdir mdbook
-        curl -Lf https://github.com/rust-lang/mdBook/releases/download/v0.4.9/mdbook-v0.4.9-x86_64-unknown-linux-gnu.tar.gz | tar -xz --directory=./mdbook
+        curl -Lf https://github.com/rust-lang/mdBook/releases/download/v0.4.26/mdbook-v0.4.26-x86_64-unknown-linux-gnu.tar.gz | tar -xz --directory=./mdbook
         echo `pwd`/mdbook >> $GITHUB_PATH
     - name: Deploy docs
       run: |
diff --git a/crates/mdman/Cargo.lock b/crates/mdman/Cargo.lock
index bb67460dd..2ce8af0d1 100644
--- a/crates/mdman/Cargo.lock
+++ b/crates/mdman/Cargo.lock
@@ -1,5 +1,7 @@
 # This file is automatically @generated by Cargo.
 # It is not intended for manual editing.
+version = 3
+
 [[package]]
 name = "ansi_term"
 version = "0.11.0"
diff --git a/crates/mdman/src/format/man.rs b/crates/mdman/src/format/man.rs
index 5df817871..9767fdd51 100644
--- a/crates/mdman/src/format/man.rs
+++ b/crates/mdman/src/format/man.rs
@@ -400,12 +400,20 @@ impl<'e> ManRenderer<'e> {
 }
 
 fn escape(s: &str) -> Result<String, Error> {
+    // Note: Possible source on output escape sequences: https://man7.org/linux/man-pages/man7/groff_char.7.html.
+    //       Otherwise, use generic escaping in the form `\[u1EE7]` or `\[u1F994]`.
+
     let mut replaced = s
         .replace('\\', "\\(rs")
         .replace('-', "\\-")
         .replace('\u{00A0}', "\\ ") // non-breaking space (non-stretchable)
         .replace('–', "\\[en]") // \u{2013} en-dash
         .replace('—', "\\[em]") // \u{2014} em-dash
+        .replace('‘', "\\[oq]") // \u{2018} left single quote
+        .replace('’', "\\[cq]") // \u{2019} right single quote or apostrophe
+        .replace('“', "\\[lq]") // \u{201C} left double quote
+        .replace('”', "\\[rq]") // \u{201D} right double quote
+        .replace('…', "\\[u2026]") // \u{2026} ellipsis
         .replace('│', "|") // \u{2502} box drawing light vertical (could use \[br])
         .replace('├', "|") // \u{251C} box drawings light vertical and right
         .replace('└', "`") // \u{2514} box drawings light up and right
@@ -413,8 +421,6 @@ fn escape(s: &str) -> Result<String, Error> {
     ;
     if replaced.starts_with('.') {
         replaced = format!("\\&.{}", &replaced[1..]);
-    } else if replaced.starts_with('\'') {
-        replaced = format!("\\(aq{}", &replaced[1..]);
     }
 
     if let Some(ch) = replaced.chars().find(|ch| {
diff --git a/crates/mdman/src/lib.rs b/crates/mdman/src/lib.rs
index 0b17be590..01c3c8d31 100644
--- a/crates/mdman/src/lib.rs
+++ b/crates/mdman/src/lib.rs
@@ -69,6 +69,7 @@ pub(crate) fn md_parser(input: &str, url: Option<Url>) -> EventIter {
     options.insert(Options::ENABLE_TABLES);
     options.insert(Options::ENABLE_FOOTNOTES);
     options.insert(Options::ENABLE_STRIKETHROUGH);
+    options.insert(Options::ENABLE_SMART_PUNCTUATION);
     let parser = Parser::new_ext(input, options);
     let parser = parser.into_offset_iter();
     // Translate all links to include the base url.
diff --git a/crates/mdman/tests/compare/expected/formatting.1 b/crates/mdman/tests/compare/expected/formatting.1
index 120859287..076c5135a 100644
--- a/crates/mdman/tests/compare/expected/formatting.1
+++ b/crates/mdman/tests/compare/expected/formatting.1
@@ -66,7 +66,7 @@ With a second paragraph inside it
 .sp
 .RS 4
 \h'-04'\(bu\h'+02'Milk
-5. Don't start at one.
+5. Don\[cq]t start at one.
 6. tamarind
 .RE
 .RE
diff --git a/crates/mdman/tests/compare/expected/formatting.txt b/crates/mdman/tests/compare/expected/formatting.txt
index 87bbb87dc..face4a3cc 100644
--- a/crates/mdman/tests/compare/expected/formatting.txt
+++ b/crates/mdman/tests/compare/expected/formatting.txt
@@ -43,7 +43,7 @@ LISTS
 
           o  Eggs
 
-          o  Milk 5. Don't start at one. 6. tamarind
+          o  Milk 5. Don’t start at one. 6. tamarind
 
        2. Second element
 
diff --git a/crates/mdman/tests/compare/expected/options.1 b/crates/mdman/tests/compare/expected/options.1
index 2d75cd25e..d362421e9 100644
--- a/crates/mdman/tests/compare/expected/options.1
+++ b/crates/mdman/tests/compare/expected/options.1
@@ -12,7 +12,7 @@ my\-command \- A brief description
 .br
 \fBmy\-command\fR (\fB\-m\fR | \fB\-M\fR) [\fIoldbranch\fR] \fInewbranch\fR
 .br
-\fBmy\-command\fR (\fB\-d\fR | \fB\-D\fR) [\fB\-r\fR] \fIbranchname\fR\&...
+\fBmy\-command\fR (\fB\-d\fR | \fB\-D\fR) [\fB\-r\fR] \fIbranchname\fR\[u2026]
 .SH "DESCRIPTION"
 A description of the command.
 .sp
@@ -49,7 +49,7 @@ Demo \fIemphasis\fR, \fBstrong\fR, ~~strike~~
 This has multiple flags.
 .RE
 .sp
-\fInamed\-arg...\fR
+\fInamed\-arg\[u2026]\fR
 .RS 4
 A named argument.
 .RE
diff --git a/crates/mdman/tests/compare/expected/options.md b/crates/mdman/tests/compare/expected/options.md
index d8b8276f6..19b0b443b 100644
--- a/crates/mdman/tests/compare/expected/options.md
+++ b/crates/mdman/tests/compare/expected/options.md
@@ -37,7 +37,7 @@ A description of the command.
 <dd class="option-desc">This has multiple flags.</dd>
 
 
-<dt class="option-term" id="option-options-named-arg..."><a class="option-anchor" href="#option-options-named-arg..."></a><em>named-arg...</em></dt>
+<dt class="option-term" id="option-options-named-arg…"><a class="option-anchor" href="#option-options-named-arg…"></a><em>named-arg…</em></dt>
 <dd class="option-desc">A named argument.</dd>
 
 
diff --git a/crates/mdman/tests/compare/expected/options.txt b/crates/mdman/tests/compare/expected/options.txt
index 32ccfd249..9bfdec67c 100644
--- a/crates/mdman/tests/compare/expected/options.txt
+++ b/crates/mdman/tests/compare/expected/options.txt
@@ -7,7 +7,7 @@ SYNOPSIS
        my-command [--abc | --xyz] name
        my-command [-f file]
        my-command (-m | -M) [oldbranch] newbranch
-       my-command (-d | -D) [-r] branchname...
+       my-command (-d | -D) [-r] branchname…
 
 DESCRIPTION
        A description of the command.
@@ -29,7 +29,7 @@ OPTIONS
        -p spec, --package spec
            This has multiple flags.
 
-       named-arg...
+       named-arg…
            A named argument.
 
    Common Options
diff --git a/src/doc/book.toml b/src/doc/book.toml
index fdbba067e..1dd1f8e0f 100644
--- a/src/doc/book.toml
+++ b/src/doc/book.toml
@@ -3,5 +3,6 @@ title = "The Cargo Book"
 author = "Alex Crichton, Steve Klabnik and Carol Nichols, with contributions from the Rust community"
 
 [output.html]
+curly-quotes = true # Enable smart-punctuation feature for more than quotes.
 git-repository-url = "https://github.com/rust-lang/cargo/tree/master/src/doc/src"
 edit-url-template = "https://github.com/rust-lang/cargo/edit/master/src/doc/{path}"
diff --git a/src/doc/contrib/book.toml b/src/doc/contrib/book.toml
index 543d58576..d6697f37f 100644
--- a/src/doc/contrib/book.toml
+++ b/src/doc/contrib/book.toml
@@ -3,6 +3,7 @@ title = "Cargo Contributor Guide"
 authors = ["Eric Huss"]
 
 [output.html]
+curly-quotes = true # Enable smart-punctuation feature for more than quotes.
 git-repository-url = "https://github.com/rust-lang/cargo/tree/master/src/doc/contrib/src"
 
 [output.html.redirect]