diff --git a/codegen/core/src/main/java/software/amazon/smithy/python/codegen/writer/MarkdownConverter.java b/codegen/core/src/main/java/software/amazon/smithy/python/codegen/writer/MarkdownConverter.java
index 30e2e003b..bdab88b4f 100644
--- a/codegen/core/src/main/java/software/amazon/smithy/python/codegen/writer/MarkdownConverter.java
+++ b/codegen/core/src/main/java/software/amazon/smithy/python/codegen/writer/MarkdownConverter.java
@@ -168,9 +168,9 @@ private static String postProcessPandocOutput(String output) {
         // Remove empty lines at the start and end
         output = output.trim();
 
-        // Remove unnecessary backslash escapes that pandoc adds for markdown
-        // These characters don't need escaping in Python docstrings
-        output = output.replaceAll("\\\\([\\[\\]'{}()<>`@_*|!~$#^])", "$1");
+        // Fix up the backslash escapes pandoc adds for Markdown so the result is
+        // a valid Python string literal (see normalizeBackslashEscapes).
+        output = normalizeBackslashEscapes(output);
 
         // Replace <note> and <important> tags with admonitions for mkdocstrings
         output = replaceAdmonitionTags(output, "note", "Note");
@@ -180,6 +180,45 @@ private static String postProcessPandocOutput(String output) {
         return output.replace("$", "$$");
     }
 
+    // A lone backslash before one of these is dropped: pandoc adds it for Markdown
+    // but it needs no escaping in a Python docstring.
+    private static final String MARKDOWN_ONLY_CHARS = "[](){}<>`@_*|!~$#^'.";
+    // A lone backslash before one of these is kept: together they form a valid
+    // Python escape. (' is intentionally left out; it lives in MARKDOWN_ONLY_CHARS.)
+    private static final String VALID_ESCAPE_CHARS = "\\\"abfnrtv01234567xNuU\r\n";
+    private static final Pattern BACKSLASH_RUN = Pattern.compile("(\\\\+)([^\\\\]|$)", Pattern.DOTALL);
+
+    /**
+     * Fixes pandoc's backslash escaping so the docstring is a valid Python literal.
+     *
+     * <p>Backslashes must come in pairs, but pandoc can leave an odd-length run
+     * (it escapes literal backslashes and Markdown characters separately, and
+     * adjacent escapes pile up). For each run we keep the pairs; a leftover
+     * backslash is then kept if it forms a valid escape, dropped if it is only
+     * there for Markdown, or doubled otherwise.
+     */
+    private static String normalizeBackslashEscapes(String output) {
+        Matcher m = BACKSLASH_RUN.matcher(output);
+        StringBuilder sb = new StringBuilder();
+        while (m.find()) {
+            int runLength = m.group(1).length();
+            String next = m.group(2);
+            int backslashes = (runLength / 2) * 2;
+            if (runLength % 2 != 0) {
+                char c = next.isEmpty() ? '\0' : next.charAt(0);
+                if (!next.isEmpty() && VALID_ESCAPE_CHARS.indexOf(c) >= 0) {
+                    backslashes += 1;
+                } else if (next.isEmpty() || MARKDOWN_ONLY_CHARS.indexOf(c) < 0) {
+                    backslashes += 2;
+                }
+                // else: Markdown-only char, drop the spurious backslash
+            }
+            m.appendReplacement(sb, Matcher.quoteReplacement("\\".repeat(backslashes) + next));
+        }
+        m.appendTail(sb);
+        return sb.toString();
+    }
+
     /**
      * Replaces admonition tags (e.g. note, important) with Google-style format.
      *
diff --git a/codegen/core/src/test/java/software/amazon/smithy/python/codegen/writer/MarkdownConverterTest.java b/codegen/core/src/test/java/software/amazon/smithy/python/codegen/writer/MarkdownConverterTest.java
index 028ec1aaf..d425f727a 100644
--- a/codegen/core/src/test/java/software/amazon/smithy/python/codegen/writer/MarkdownConverterTest.java
+++ b/codegen/core/src/test/java/software/amazon/smithy/python/codegen/writer/MarkdownConverterTest.java
@@ -128,6 +128,54 @@ public void testConvertRemovesUnnecessaryBackslashEscapes() {
         assertEquals("Text with [brackets] and {braces} and (parens)", result.trim());
     }
 
+    @Test
+    public void testConvertPreservesLiteralDoubleBackslash() {
+        // A literal "\\" is a valid Python escape (e.g. a password charset like
+        // "[\\]") and must be preserved.
+        String html = "<code>@[\\\\]^</code>";
+        String result = MarkdownConverter.convert(html, createMockContext(true)).trim();
+        assertEquals("`@[\\\\]^`", result);
+    }
+
+    @Test
+    public void testConvertEscapesLoneBackslash() {
+        // A lone backslash that is not part of a recognized Python escape (here a
+        // backslash followed by a space) must be doubled so the docstring is a
+        // valid Python string.
+        String html = "<code>[ \\ ]</code>";
+        String result = MarkdownConverter.convert(html, createMockContext(true)).trim();
+        assertEquals("`[ \\\\ ]`", result);
+    }
+
+    @Test
+    public void testConvertPreservesValidPythonEscapes() {
+        // A backslash that already forms a valid Python escape (e.g. \") must be
+        // left untouched rather than doubled.
+        String html = "<code>!\\\"#</code>";
+        String result = MarkdownConverter.convert(html, createMockContext(true)).trim();
+        assertEquals("`!\\\"#`", result);
+    }
+
+    @Test
+    public void testConvertHandlesBackslashBeforeMarkdownChar() {
+        // A backslash followed by a Markdown-significant character (here "*") makes
+        // pandoc emit an odd-length backslash run. The spurious escape must be
+        // dropped so the result is valid Python.
+        String html = "<code>arn:aws:iam::\\*:user/\\*</code>";
+        String result = MarkdownConverter.convert(html, createMockContext(true)).trim();
+        assertEquals("`arn:aws:iam::*:user/*`", result);
+    }
+
+    @Test
+    public void testConvertHandlesBackslashStarNextToQuote() {
+        // The API Gateway model documents the comment marker "\*/". Next to a quote,
+        // pandoc emits an odd-length backslash run; the result must stay a valid
+        // Python literal.
+        String html = "<p>Do not include \"\\*/\" characters</p>";
+        String result = MarkdownConverter.convert(html, createMockContext(true)).trim();
+        assertEquals("Do not include \\\"\\\\*/\\\" characters", result);
+    }
+
     @Test
     public void testConvertMixedElements() {
         String html = "<h1>Title</h1><p>Paragraph</p><ul><li>Item 1</li><li>Item 2</li></ul>";