diff --git a/dotenv/parse.ts b/dotenv/parse.ts
index 63d25b3c8fef..28e26e3316c8 100644
--- a/dotenv/parse.ts
+++ b/dotenv/parse.ts
@@ -8,7 +8,7 @@ type LineParseResult = {
 };
 
 const KEY_VALUE_REGEXP =
-  /^\s*(?:export\s+)?(?<key>[^\s=#]+?)\s*=[\ \t]*('\r?\n?(?<notInterpolated>(.|\r\n|\n)*?)\r?\n?'|"\r?\n?(?<interpolated>(.|\r\n|\n)*?)\r?\n?"|(?<unquoted>[^\r\n#]*)) *#*.*$/gm;
+  /^\s*(?:export\s+)?(?<key>[^\s=#]+?)\s*=[\ \t]*('\r?\n?(?<notInterpolated>(?:.|\r\n|\n)*?)\r?\n?'|"\r?\n?(?<interpolated>(?:[^"\\]|\\.)*)\r?\n?"|(?<unquoted>[^\r\n#]*)) *#*.*$/gm;
 
 const VALID_KEY_REGEXP = /^[a-zA-Z_][a-zA-Z0-9_]*$/;
 
@@ -19,11 +19,13 @@ const CHARACTERS_MAP: { [key: string]: string } = {
   "\\n": "\n",
   "\\r": "\r",
   "\\t": "\t",
+  '\\"': '"',
+  "\\\\": "\\",
 };
 
 function expandCharacters(str: string): string {
   return str.replace(
-    /\\([nrt])/g,
+    /\\([nrt"\\])/g,
     ($1: keyof typeof CHARACTERS_MAP): string => CHARACTERS_MAP[$1] ?? "",
   );
 }
diff --git a/dotenv/parse_test.ts b/dotenv/parse_test.ts
index e825b9728284..2d94d4a45e99 100644
--- a/dotenv/parse_test.ts
+++ b/dotenv/parse_test.ts
@@ -284,3 +284,42 @@ Deno.test("parse() result is not affected by extended Object.prototype", () => {
   assertEquals(result.foo, undefined);
   assertEquals(result.bar, "1");
 });
+
+Deno.test("parse() round-trips through stringify()", async (t) => {
+  const { stringify } = await import("./stringify.ts");
+
+  await t.step("basic value", () => {
+    const original = { HELLO: "world" };
+    assertEquals(parse(stringify(original)), original);
+  });
+
+  await t.step("value with spaces", () => {
+    const original = { GREETING: "hello world" };
+    assertEquals(parse(stringify(original)), original);
+  });
+
+  await t.step("value with single quote", () => {
+    const original = { PARSE: "par'se" };
+    assertEquals(parse(stringify(original)), original);
+  });
+
+  await t.step("value with double quote (JSON-like)", () => {
+    const original = { JSON: '{"key":"value"}' };
+    assertEquals(parse(stringify(original)), original);
+  });
+
+  await t.step("value with both quote types", () => {
+    const original = { MIXED: `a'b"c` };
+    assertEquals(parse(stringify(original)), original);
+  });
+
+  await t.step("value with newline", () => {
+    const original = { MULTILINE: "hello\nworld" };
+    assertEquals(parse(stringify(original)), original);
+  });
+
+  await t.step("value with backslash and quotes", () => {
+    const original = { BS: String.raw`test\"value` };
+    assertEquals(parse(stringify(original)), original);
+  });
+});
diff --git a/dotenv/stringify.ts b/dotenv/stringify.ts
index 63539cf7e3b4..c1bd67ec113c 100644
--- a/dotenv/stringify.ts
+++ b/dotenv/stringify.ts
@@ -19,7 +19,7 @@
 export function stringify(object: Record<string, string>): string {
   const lines: string[] = [];
   for (const [key, value] of Object.entries(object)) {
-    let quote;
+    let quote: string | undefined;
 
     let escapedValue = value ?? "";
     if (key.startsWith("#")) {
@@ -28,11 +28,21 @@ export function stringify(object: Record<string, string>): string {
         `key starts with a '#' indicates a comment and is ignored: '${key}'`,
       );
       continue;
-    } else if (escapedValue.includes("\n") || escapedValue.includes("'")) {
-      // escape inner new lines
-      escapedValue = escapedValue.replaceAll("\n", "\\n");
+    }
+
+    const hasNewline = escapedValue.includes("\n");
+    const hasSingleQuote = escapedValue.includes("'");
+    const hasDoubleQuote = escapedValue.includes('"');
+
+    // Use double quotes when the value contains newlines (so they can be
+    // expanded back) or single quotes (which are safe inside double quotes).
+    if (hasNewline || hasSingleQuote) {
       quote = `"`;
-    } else if (escapedValue.match(/\W/)) {
+      // Escape backslashes first so that existing backslashes are not
+      // confused with escape sequences when parsed.
+      escapedValue = escapedValue.replaceAll("\\", "\\\\");
+      if (hasNewline) escapedValue = escapedValue.replaceAll("\n", "\\n");
+    } else if (hasDoubleQuote || escapedValue.match(/\W/)) {
       quote = "'";
     }
 
diff --git a/dotenv/stringify_test.ts b/dotenv/stringify_test.ts
index b24a17b1794c..dc03e2367793 100644
--- a/dotenv/stringify_test.ts
+++ b/dotenv/stringify_test.ts
@@ -83,4 +83,24 @@ Deno.test("stringify()", async (t) => {
       stringify({ PARSE: "par'se" }),
       `PARSE="par'se"`,
     ));
+  await t.step("handles double-quote characters", () =>
+    assertEquals(
+      stringify({ JSON: '{"key":"value"}' }),
+      `JSON='{"key":"value"}'`,
+    ));
+  await t.step("handles both quote characters", () =>
+    assertEquals(
+      stringify({ MIXED: `a'b"c` }),
+      `MIXED="a'b\\"c"`,
+    ));
+  await t.step("handles backslash with double quotes", () =>
+    assertEquals(
+      stringify({ BS: String.raw`test\"value` }),
+      `BS="test\\\\\\"value"`,
+    ));
+  await t.step("handles newline with single quotes", () =>
+    assertEquals(
+      stringify({ NL: "hello\nit's me" }),
+      `NL="hello\\nit's me"`,
+    ));
 });