diff --git a/src/index.ts b/src/index.ts
index d2b7df7..f174cca 100644
--- a/src/index.ts
+++ b/src/index.ts
@@ -1,5 +1,82 @@
-import YAML from "yaml";
-const FRONTMATTER_REGEX = /^---[\s\S]*?---/gm;
+import YAML, { YAMLError } from "yaml";
+
+export type EMDYData = Record<string, unknown>;
+
+type Mode = "yaml" | "markdown";
+interface PendingDocument {
+  content: string;
+  markdownKey: string;
+}
+
+export class EMDYError extends Error {
+  name = "EMDYError";
+}
+
+export class EMDYParseError extends EMDYError {
+  name = "EMDYParseError";
+  original?: Error;
+
+  constructor(message: string, original?: Error) {
+    super(`EMDY Parse Error: ${message}`);
+    this.original = original;
+  }
+}
+
+/**
+ * Parse a single PendingDocument into EMDYData
+ * @param document The PendingDocument to parse
+ * @returns The parsed EMDYData
+ */
+function parseDocument(document: PendingDocument): EMDYData {
+  const yamlLines: string[] = [];
+  const markdownLines: string[] = [];
+  const contentLines = document.content.trim().split("\n");
+
+  let mode: Mode = "markdown";
+
+  for (const line of contentLines) {
+    // Handle boundary lines
+    if (line.trim() === "---") {
+      // Upon encountering a boundary in YAML mode, switch to markdown mode
+      if (mode === "yaml") {
+        mode = "markdown";
+      }
+
+      // When in markdown mode (default), only switch to YAML mode
+      // if no markdown has been collected yet. This ensures that
+      // YAML frontmatter is only parsed if it exists at the start of the document.
+      else if (mode === "markdown" && markdownLines.length === 0) {
+        mode = "yaml";
+      }
+
+      // Continue the loop to skip the boundary line
+      continue;
+    }
+
+    // Handle content lines
+    if (mode === "yaml") {
+      yamlLines.push(line);
+    } else {
+      markdownLines.push(line);
+    }
+  }
+
+  const yamlContent = yamlLines.join("\n").trim();
+  const markdownContent = markdownLines.join("\n").trim();
+
+  try {
+    return {
+      ...YAML.parse(yamlContent || "{}"),
+      [document.markdownKey]: markdownContent,
+    };
+  } catch (error) {
+    if (error instanceof YAMLError) {
+      throw new EMDYParseError("Failed to parse YAML frontmatter", error);
+    }
+
+    throw new EMDYError(`An unexpected error occured: ${error}`);
+  }
+}
 
 /**
  * Parse a markdown document with optional YAML frontmatter into an object
@@ -8,23 +85,8 @@ const FRONTMATTER_REGEX = /^---[\s\S]*?---/gm;
  * @param markdownKey The key to use for the markdown content
  * @returns The parsed markdown content and frontmatter
  */
-function parse(
-  content: string,
-  markdownKey = "content",
-): Record<string, unknown> {
-  const markdown = content.trim().replace(FRONTMATTER_REGEX, "").trim();
-  let frontmatter: Record<string, unknown> = {};
-
-  if (FRONTMATTER_REGEX.test(content)) {
-    const frontmatterString = content.match(FRONTMATTER_REGEX)?.[0] ?? "";
-    const cleanFrontmatter = frontmatterString.replaceAll("---", "").trim();
-    frontmatter = YAML.parse(cleanFrontmatter);
-  }
-
-  return {
-    [markdownKey]: markdown,
-    ...frontmatter,
-  };
+export function parse(content: string, markdownKey = "content"): EMDYData {
+  return parseDocument({ content, markdownKey });
 }
 
 /**
@@ -34,7 +96,7 @@ function parse(
  * @param markdownKey The key to use for the markdown content
  * @returns The parsed markdown content and frontmatter
  */
-function stringify(
+export function stringify(
   data: Record<string, unknown>,
   markdownKey = "content",
 ): string {
@@ -50,11 +112,54 @@ function stringify(
 
   const stringifiedFrontmatter = YAML.stringify(frontmatter).trim();
 
-  return `---\n${stringifiedFrontmatter}\n---\n${markdown}`;
+  return `
+---
+${stringifiedFrontmatter}
+---
+${markdown}
+`.trim();
+}
+
+/**
+ * Parse a multi-document file into an array of EMDYData objects
+ * @param content The raw markdown content containing multiple documents
+ * @param markdownKey The key to use for the markdown content in each document
+ * @returns An array of parsed EMDYData objects
+ */
+export function parseAll(content: string, markdownKey = "content"): EMDYData[] {
+  const documents: PendingDocument[] = [];
+  const lines = content.split("\n");
+
+  let currentDoc: string[] = [];
+
+  for (const line of lines) {
+    if (line.trim().startsWith("===") && currentDoc.length > 0) {
+      documents.push({
+        content: currentDoc.join("\n").trim(),
+        markdownKey,
+      });
+      currentDoc = [];
+      continue;
+    }
+
+    currentDoc.push(line);
+  }
+
+  // Add any remaining content as the last document
+  if (currentDoc.length > 0) {
+    documents.push({
+      content: currentDoc.join("\n").trim(),
+      markdownKey,
+    });
+  }
+
+  // Split by document boundaries
+  return documents.map(parseDocument);
 }
 
 const EMDY = {
   parse,
+  parseAll,
   stringify,
 } as const;
 
diff --git a/src/test/emdy.test.ts b/src/test/emdy.test.ts
index 4291bf8..0abe941 100644
--- a/src/test/emdy.test.ts
+++ b/src/test/emdy.test.ts
@@ -1,5 +1,5 @@
 import { describe, expect, test } from "bun:test";
-import EMDY from "../index";
+import EMDY, { EMDYParseError } from "../index";
 
 describe(EMDY.parse, () => {
   test("parses markdown content without frontmatter", () => {
@@ -31,6 +31,19 @@ And here is the content
       content: "And here is the content",
     });
   });
+
+  test("throws an EMDYParseError for invalid frontmatter", () => {
+    const content = `---
+key:
+anothe
+---
+
+stuff`;
+
+    expect(() => {
+      EMDY.parse(content);
+    }).toThrow(EMDYParseError);
+  });
 });
 
 describe(EMDY.stringify, () => {
@@ -65,3 +78,54 @@ describe(EMDY.stringify, () => {
     );
   });
 });
+
+describe(EMDY.parseAll, () => {
+  test("parses multiple emdy documents", () => {
+    const content = `---
+hello: world
+goodbye: world
+---
+
+some markdown
+===
+another document
+===
+---
+more frontmatter: yep
+---
+
+and how
+`.trim();
+
+    const parsed = EMDY.parseAll(content);
+    expect(parsed).toEqual([
+      {
+        hello: "world",
+        goodbye: "world",
+        content: "some markdown",
+      },
+      {
+        content: "another document",
+      },
+      {
+        "more frontmatter": "yep",
+        content: "and how",
+      },
+    ]);
+  });
+
+  test("parses a single emdy document", () => {
+    const content = `---
+hello: world
+---
+example!
+`;
+
+    expect(EMDY.parseAll(content)).toEqual([
+      {
+        hello: "world",
+        content: "example!",
+      },
+    ]);
+  });
+});