diff --git a/packages/editor/core/src/styles/editor.css b/packages/editor/core/src/styles/editor.css
index b0d2a1021..d0ab0fce8 100644
--- a/packages/editor/core/src/styles/editor.css
+++ b/packages/editor/core/src/styles/editor.css
@@ -123,7 +123,7 @@ ul[data-type="taskList"] li[data-checked="true"] > div > p {
   outline: none;
   cursor: text;
   line-height: 1.2;
-  font-family: inherit;
+  font-family: "system-ui";
   font-size: 14px;
   color: inherit;
   -moz-box-sizing: border-box;
diff --git a/packages/editor/core/src/ui/extensions/index.tsx b/packages/editor/core/src/ui/extensions/index.tsx
index 5bfba3b0f..190731fe0 100644
--- a/packages/editor/core/src/ui/extensions/index.tsx
+++ b/packages/editor/core/src/ui/extensions/index.tsx
@@ -25,7 +25,8 @@ import { DeleteImage } from "src/types/delete-image";
 import { IMentionSuggestion } from "src/types/mention-suggestion";
 import { RestoreImage } from "src/types/restore-image";
 import { CustomLinkExtension } from "src/ui/extensions/custom-link";
-import { CustomCodeInlineExtension } from "./code-inline";
+import { CustomCodeInlineExtension } from "src/ui/extensions/code-inline";
+import { CustomTypographyExtension } from "src/ui/extensions/typography";
 
 export const CoreEditorExtensions = (
   mentionConfig: {
@@ -79,6 +80,7 @@ export const CoreEditorExtensions = (
         "text-custom-primary-300 underline underline-offset-[3px] hover:text-custom-primary-500 transition-colors cursor-pointer",
     },
   }),
+  CustomTypographyExtension,
   ImageExtension(deleteFile, restoreFile, cancelUploadImage).configure({
     HTMLAttributes: {
       class: "rounded-lg border border-custom-border-300",
diff --git a/packages/editor/core/src/ui/extensions/typography/index.ts b/packages/editor/core/src/ui/extensions/typography/index.ts
new file mode 100644
index 000000000..78af3c46e
--- /dev/null
+++ b/packages/editor/core/src/ui/extensions/typography/index.ts
@@ -0,0 +1,109 @@
+import { Extension } from "@tiptap/core";
+import {
+  TypographyOptions,
+  emDash,
+  ellipsis,
+  leftArrow,
+  rightArrow,
+  copyright,
+  trademark,
+  servicemark,
+  registeredTrademark,
+  oneHalf,
+  plusMinus,
+  notEqual,
+  laquo,
+  raquo,
+  multiplication,
+  superscriptTwo,
+  superscriptThree,
+  oneQuarter,
+  threeQuarters,
+  impliesArrowRight,
+} from "src/ui/extensions/typography/inputRules";
+
+export const CustomTypographyExtension = Extension.create<TypographyOptions>({
+  name: "typography",
+
+  addInputRules() {
+    const rules = [];
+
+    if (this.options.emDash !== false) {
+      rules.push(emDash(this.options.emDash));
+    }
+
+    if (this.options.impliesArrowRight !== false) {
+      rules.push(impliesArrowRight(this.options.impliesArrowRight));
+    }
+
+    if (this.options.ellipsis !== false) {
+      rules.push(ellipsis(this.options.ellipsis));
+    }
+
+    if (this.options.leftArrow !== false) {
+      rules.push(leftArrow(this.options.leftArrow));
+    }
+
+    if (this.options.rightArrow !== false) {
+      rules.push(rightArrow(this.options.rightArrow));
+    }
+
+    if (this.options.copyright !== false) {
+      rules.push(copyright(this.options.copyright));
+    }
+
+    if (this.options.trademark !== false) {
+      rules.push(trademark(this.options.trademark));
+    }
+
+    if (this.options.servicemark !== false) {
+      rules.push(servicemark(this.options.servicemark));
+    }
+
+    if (this.options.registeredTrademark !== false) {
+      rules.push(registeredTrademark(this.options.registeredTrademark));
+    }
+
+    if (this.options.oneHalf !== false) {
+      rules.push(oneHalf(this.options.oneHalf));
+    }
+
+    if (this.options.plusMinus !== false) {
+      rules.push(plusMinus(this.options.plusMinus));
+    }
+
+    if (this.options.notEqual !== false) {
+      rules.push(notEqual(this.options.notEqual));
+    }
+
+    if (this.options.laquo !== false) {
+      rules.push(laquo(this.options.laquo));
+    }
+
+    if (this.options.raquo !== false) {
+      rules.push(raquo(this.options.raquo));
+    }
+
+    if (this.options.multiplication !== false) {
+      rules.push(multiplication(this.options.multiplication));
+    }
+
+    if (this.options.superscriptTwo !== false) {
+      rules.push(superscriptTwo(this.options.superscriptTwo));
+    }
+
+    if (this.options.superscriptThree !== false) {
+      rules.push(superscriptThree(this.options.superscriptThree));
+    }
+
+    if (this.options.oneQuarter !== false) {
+      rules.push(oneQuarter(this.options.oneQuarter));
+    }
+
+    if (this.options.threeQuarters !== false) {
+      rules.push(threeQuarters(this.options.threeQuarters));
+    }
+
+    return rules;
+  },
+});
diff --git a/packages/editor/core/src/ui/extensions/typography/inputRules.ts b/packages/editor/core/src/ui/extensions/typography/inputRules.ts
new file mode 100644
index 000000000..f528e9242
--- /dev/null
+++ b/packages/editor/core/src/ui/extensions/typography/inputRules.ts
@@ -0,0 +1,137 @@
+import { textInputRule } from "@tiptap/core";
+
+export interface TypographyOptions {
+  emDash: false | string;
+  ellipsis: false | string;
+  leftArrow: false | string;
+  rightArrow: false | string;
+  copyright: false | string;
+  trademark: false | string;
+  servicemark: false | string;
+  registeredTrademark: false | string;
+  oneHalf: false | string;
+  plusMinus: false | string;
+  notEqual: false | string;
+  laquo: false | string;
+  raquo: false | string;
+  multiplication: false | string;
+  superscriptTwo: false | string;
+  superscriptThree: false | string;
+  oneQuarter: false | string;
+  threeQuarters: false | string;
+  impliesArrowRight: false | string;
+}
+
+export const emDash = (override?: string) =>
+  textInputRule({
+    find: /--$/,
+    replace: override ?? "—",
+  });
+
+export const impliesArrowRight = (override?: string) =>
+  textInputRule({
+    find: /=>$/,
+    replace: override ?? "⇒",
+  });
+
+export const leftArrow = (override?: string) =>
+  textInputRule({
+    find: /<-$/,
+    replace: override ?? "←",
+  });
+
+export const rightArrow = (override?: string) =>
+  textInputRule({
+    find: /->$/,
+    replace: override ?? "→",
+  });
+
+export const ellipsis = (override?: string) =>
+  textInputRule({
+    find: /\.\.\.$/,
+    replace: override ?? "…",
+  });
+
+export const copyright = (override?: string) =>
+  textInputRule({
+    find: /\(c\)$/,
+    replace: override ?? "©",
+  });
+
+export const trademark = (override?: string) =>
+  textInputRule({
+    find: /\(tm\)$/,
+    replace: override ?? "™",
+  });
+
+export const servicemark = (override?: string) =>
+  textInputRule({
+    find: /\(sm\)$/,
+    replace: override ?? "℠",
+  });
+
+export const registeredTrademark = (override?: string) =>
+  textInputRule({
+    find: /\(r\)$/,
+    replace: override ?? "®",
+  });
+
+export const oneHalf = (override?: string) =>
+  textInputRule({
+    find: /(?:^|\s)(1\/2)\s$/,
+    replace: override ?? "½",
+  });
+
+export const plusMinus = (override?: string) =>
+  textInputRule({
+    find: /\+\/-$/,
+    replace: override ?? "±",
+  });
+
+export const notEqual = (override?: string) =>
+  textInputRule({
+    find: /!=$/,
+    replace: override ?? "≠",
+  });
+
+export const laquo = (override?: string) =>
+  textInputRule({
+    find: /<<$/,
+    replace: override ?? "«",
+  });
+
+export const raquo = (override?: string) =>
+  textInputRule({
+    find: />>$/,
+    replace: override ?? "»",
+  });
+
+export const multiplication = (override?: string) =>
+  textInputRule({
+    find: /\d+\s?([*x])\s?\d+$/,
+    replace: override ?? "×",
+  });
+
+export const superscriptTwo = (override?: string) =>
+  textInputRule({
+    find: /\^2$/,
+    replace: override ?? "²",
+  });
+
+export const superscriptThree = (override?: string) =>
+  textInputRule({
+    find: /\^3$/,
+    replace: override ?? "³",
+  });
+
+export const oneQuarter = (override?: string) =>
+  textInputRule({
+    find: /(?:^|\s)(1\/4)\s$/,
+    replace: override ?? "¼",
+  });
+
+export const threeQuarters = (override?: string) =>
+  textInputRule({
+    find: /(?:^|\s)(3\/4)\s$/,
+    replace: override ?? "¾",
+  });