diff --git a/app/assets/javascripts/discourse/tests/unit/lib/pretty-text-test.js b/app/assets/javascripts/discourse/tests/unit/lib/pretty-text-test.js
index a02cf063b22..86e2fd72d75 100644
--- a/app/assets/javascripts/discourse/tests/unit/lib/pretty-text-test.js
+++ b/app/assets/javascripts/discourse/tests/unit/lib/pretty-text-test.js
@@ -1601,4 +1601,74 @@ var bar = 'bar';
     assert.cookedOptions(" -->asd ", enabledTypographer, "<p>–&gt;asd</p>");
     assert.cookedOptions(" -->asd", enabledTypographer, "<p>–&gt;asd</p>");
   });
+
+  test("default typhographic replacements", function (assert) {
+    const enabledTypographer = {
+      siteSettings: { enable_markdown_typographer: true },
+    };
+
+    assert.cookedOptions("(bad)", enabledTypographer, "<p>(bad)</p>");
+    assert.cookedOptions("+-5", enabledTypographer, "<p>±5</p>");
+    assert.cookedOptions(
+      "test.. test... test..... test?..... test!....",
+      enabledTypographer,
+      "<p>test… test… test… test?.. test!..</p>"
+    );
+    assert.cookedOptions(
+      "!!!!!! ???? ,,",
+      enabledTypographer,
+      "<p>!!! ??? ,</p>"
+    );
+    assert.cookedOptions(
+      "!!!!!! ???? ,,",
+      enabledTypographer,
+      "<p>!!! ??? ,</p>"
+    );
+    assert.cookedOptions("(tm) (TM)", enabledTypographer, "<p>™ ™</p>");
+  });
+
+  test("default typhographic replacements - dashes", function (assert) {
+    const enabledTypographer = {
+      siteSettings: { enable_markdown_typographer: true },
+    };
+
+    assert.cookedOptions(
+      "---markdownit --- super---",
+      enabledTypographer,
+      "<p>—markdownit — super—</p>"
+    );
+    assert.cookedOptions(
+      "markdownit---awesome",
+      enabledTypographer,
+      "<p>markdownit—awesome</p>"
+    );
+    assert.cookedOptions("abc ----", enabledTypographer, "<p>abc ----</p>");
+    assert.cookedOptions(
+      "--markdownit -- super--",
+      enabledTypographer,
+      "<p>–markdownit – super–</p>"
+    );
+    assert.cookedOptions(
+      "markdownit--awesome",
+      enabledTypographer,
+      "<p>markdownit–awesome</p>"
+    );
+    assert.cookedOptions("1---2---3", enabledTypographer, "<p>1—2—3</p>");
+    assert.cookedOptions("1--2--3", enabledTypographer, "<p>1–2–3</p>");
+    assert.cookedOptions(
+      "<p>1 – – 3</p>",
+      enabledTypographer,
+      "<p>1 – – 3</p>"
+    );
+  });
+
+  test("disabled typhographic replacements", function (assert) {
+    const enabledTypographer = {
+      siteSettings: { enable_markdown_typographer: true },
+    };
+
+    assert.cookedOptions("(c) (C)", enabledTypographer, "<p>(c) (C)</p>");
+    assert.cookedOptions("(r) (R)", enabledTypographer, "<p>(r) (R)</p>");
+    assert.cookedOptions("(p) (P)", enabledTypographer, "<p>(p) (P)</p>");
+  });
 });
diff --git a/app/assets/javascripts/pretty-text/engines/discourse-markdown/custom-typographer-replacements.js b/app/assets/javascripts/pretty-text/engines/discourse-markdown/custom-typographer-replacements.js
new file mode 100644
index 00000000000..220e75fe275
--- /dev/null
+++ b/app/assets/javascripts/pretty-text/engines/discourse-markdown/custom-typographer-replacements.js
@@ -0,0 +1,95 @@
+// Simple typographic replacements
+//
+// (tm) (TM) → ™
+// +- → ±
+// ... → … (also ?.... → ?.., !.... → !..)
+// ???????? → ???, !!!!! → !!!, `,,` → `,`
+// -- → &ndash;, --- → &mdash;
+// --> <-- -> <- to → ← → ←
+//
+// Disabled replacements:
+//
+// (c) (C) → ©
+// (r) (R) → ®
+// (p) (P) -> §
+
+let RARE_RE = /\+-|\.\.|\?\?\?\?|!!!!|,,|--|-->|<--|->|<-/;
+let SCOPED_ABBR_RE = /\((tm)\)/gi;
+
+function replaceScoped(inlineTokens) {
+  let i, token;
+
+  for (i = inlineTokens.length - 1; i >= 0; i--) {
+    token = inlineTokens[i];
+    if (token.type === "text") {
+      token.content = token.content.replace(SCOPED_ABBR_RE, () => {
+        return "™";
+      });
+    }
+  }
+}
+
+function replaceRare(inlineTokens) {
+  let i,
+    token,
+    inside_autolink = 0;
+
+  for (i = inlineTokens.length - 1; i >= 0; i--) {
+    token = inlineTokens[i];
+
+    if (token.type === "text" && !inside_autolink) {
+      if (RARE_RE.test(token.content)) {
+        token.content = token.content
+          .replace(/\+-/g, "±")
+          // Custom arrows
+          .replace(/(^|\s)-{1,2}>(\s|$)/gm, "\u0020\u2192\u0020")
+          .replace(/(^|\s)<-{1,2}(\s|$)/gm, "\u0020\u2190\u0020")
+          // .., ..., ....... -> …
+          // but ?..... & !..... -> ?.. & !..
+          .replace(/\.{2,}/g, "…")
+          .replace(/([?!])…/g, "$1..")
+          .replace(/([?!]){4,}/g, "$1$1$1")
+          .replace(/,{2,}/g, ",")
+          // em-dash
+          .replace(/(^|[^-])---(?=[^-]|$)/gm, "$1\u2014")
+          // en-dash
+          .replace(/(^|\s)--(?=\s|$)/gm, "$1\u2013")
+          .replace(/(^|[^-\s])--(?=[^-\s]|$)/gm, "$1\u2013");
+      }
+    }
+
+    if (token.type === "link_open" && token.info === "auto") {
+      inside_autolink--;
+    }
+
+    if (token.type === "link_close" && token.info === "auto") {
+      inside_autolink++;
+    }
+  }
+}
+
+function replace(state) {
+  let blkIdx;
+
+  for (blkIdx = state.tokens.length - 1; blkIdx >= 0; blkIdx--) {
+    if (state.tokens[blkIdx].type !== "inline") {
+      continue;
+    }
+
+    if (SCOPED_ABBR_RE.test(state.tokens[blkIdx].content)) {
+      replaceScoped(state.tokens[blkIdx].children);
+    }
+
+    if (RARE_RE.test(state.tokens[blkIdx].content)) {
+      replaceRare(state.tokens[blkIdx].children);
+    }
+  }
+}
+
+export function setup(helper) {
+  helper.registerPlugin((md) => {
+    if (md.options.typographer) {
+      md.core.ruler.at("replacements", replace);
+    }
+  });
+}
diff --git a/app/assets/javascripts/pretty-text/engines/discourse-markdown/typographer-arrows.js b/app/assets/javascripts/pretty-text/engines/discourse-markdown/typographer-arrows.js
deleted file mode 100644
index b63f52f8969..00000000000
--- a/app/assets/javascripts/pretty-text/engines/discourse-markdown/typographer-arrows.js
+++ /dev/null
@@ -1,32 +0,0 @@
-function replaceArrows(state) {
-  for (let i = 0; i < state.tokens.length; i++) {
-    let token = state.tokens[i];
-
-    if (token.type !== "inline") {
-      continue;
-    }
-
-    const arrowsRegexp = /-->|<--|->|<-/;
-    if (arrowsRegexp.test(token.content)) {
-      for (let ci = 0; ci < token.children.length; ci++) {
-        let child = token.children[ci];
-
-        if (child.type === "text") {
-          if (arrowsRegexp.test(child.content)) {
-            child.content = child.content
-              .replace(/(^|\s)-{1,2}>(\s|$)/gm, "\u0020\u2192\u0020")
-              .replace(/(^|\s)<-{1,2}(\s|$)/gm, "\u0020\u2190\u0020");
-          }
-        }
-      }
-    }
-  }
-}
-
-export function setup(helper) {
-  helper.registerPlugin((md) => {
-    if (md.options.typographer) {
-      md.core.ruler.before("replacements", "typographer-arrow", replaceArrows);
-    }
-  });
-}
diff --git a/spec/components/pretty_text_spec.rb b/spec/components/pretty_text_spec.rb
index c0ae2ac6a05..e154b54bb9f 100644
--- a/spec/components/pretty_text_spec.rb
+++ b/spec/components/pretty_text_spec.rb
@@ -1442,10 +1442,10 @@ HTML
 
   it 'supports typographer' do
     SiteSetting.enable_markdown_typographer = true
-    expect(PrettyText.cook('(tm)')).to eq('<p>™</p>')
+    expect(PrettyText.cook('->')).to eq('<p> → </p>')
 
     SiteSetting.enable_markdown_typographer = false
-    expect(PrettyText.cook('(tm)')).to eq('<p>(tm)</p>')
+    expect(PrettyText.cook('->')).to eq('<p>-&gt;</p>')
   end
 
   it 'uses quotation marks from site settings' do