diff --git a/__tests__/ExpensiMark-Markdown-test.js b/__tests__/ExpensiMark-Markdown-test.js
index bb1baf1ff..896b3f189 100644
--- a/__tests__/ExpensiMark-Markdown-test.js
+++ b/__tests__/ExpensiMark-Markdown-test.js
@@ -23,6 +23,18 @@ test('Test multi-line bold HTML replacement', () => {
     expect(parser.htmlToMarkdown(testString)).toBe(replacedString);
 });
 
+test('Converts <b> tags with font-weight 700 inline style in between to markdown bold', () => {
+    const input = '<b><span style="font-weight:400;">This is a text with </span><span style="font-weight:700;">nested bold</span><span style="font-weight:400;"> content</span></b>';
+    const expected = 'This is a text with *nested bold* content';
+    expect(parser.htmlToMarkdown(input)).toBe(expected);
+});
+
+test('Does not convert <b> tags with font-weight normal inline style to markdown bold', () => {
+    const input = '<b><span style="font-weight:400;">This is a text with </span><span style="font-weight:normal;">no bold</span><span style="font-weight:400;"> content</span></b>';
+    const expected = 'This is a text with no bold content';
+    expect(parser.htmlToMarkdown(input)).toBe(expected);
+});
+
 test('Test italic HTML replacement', () => {
     const italicTestStartString = 'This is a <em>sentence,</em> and it has some <em>punctuation, words, and spaces</em>. <em>test</em> _ testing_ test_test_test. _ test _ _test _ '
         + 'This is a <i>sentence,</i> and it has some <i>punctuation, words, and spaces</i>. <i>test</i> _ testing_ test_test_test. _ test _ _test _';
diff --git a/lib/ExpensiMark.ts b/lib/ExpensiMark.ts
index 04735ce2a..74e76dcd6 100644
--- a/lib/ExpensiMark.ts
+++ b/lib/ExpensiMark.ts
@@ -546,14 +546,33 @@ export default class ExpensiMark {
             },
             {
                 name: 'bold',
-                regex: /<(b|strong)(?:"[^"]*"|'[^']*'|[^'">])*>([\s\S]*?)<\/\1>(?![^<]*(<\/pre>|<\/code>))/gi,
-                replacement: (match, tagContent, innerContent) => {
-                    const fontWeightMatch = innerContent.match(/style="(.*?)"/);
-                    const isFontWeightBold = fontWeightMatch
-                        ? fontWeightMatch[1].replaceAll(/\s/g, '').includes('font-weight:bold;') || fontWeightMatch[1].replaceAll(/\s/g, '').includes('font-weight:700;')
-                        : false;
-                    const isBold = fontWeightMatch ? isFontWeightBold : true;
-                    return isBold ? `*${innerContent}*` : innerContent;
+                regex: /<(b|strong|span)(?:"[^"]*"|'[^']*'|[^'">])*>([\s\S]*?)<\/\1>(?![^<]*(<\/pre>|<\/code>))/gi,
+                replacement: (extras, match, tagName, innerContent) => {
+                    // To check if style attribute contains bold font-weight
+                    const isBoldFromStyle = (style: string | null) => {
+                        return style ? style.replace(/\s/g, '').includes('font-weight:bold;') || style.replace(/\s/g, '').includes('font-weight:700;') : false;
+                    };
+
+                    const updateSpacesAndWrapWithAsterisksIfBold = (content: string, isBold: boolean) => {
+                        const trimmedContent = content.trim();
+                        const leadingSpace = content.startsWith(' ') ? ' ' : '';
+                        const trailingSpace = content.endsWith(' ') ? ' ' : '';
+                        return isBold ? `${leadingSpace}*${trimmedContent}*${trailingSpace}` : content;
+                    };
+
+                    // Determine if the outer tag is bold
+                    const styleAttributeMatch = match.match(/style="(.*?)"/);
+                    const isFontWeightBold = isBoldFromStyle(styleAttributeMatch ? styleAttributeMatch[1] : null);
+                    const isBold = styleAttributeMatch ? isFontWeightBold : tagName === 'b' || tagName === 'strong';
+
+                    // Process nested spans with potential bold style
+                    const processedInnerContent = innerContent.replace(/<span(?:"[^"]*"|'[^']*'|[^'">])*>([\s\S]*?)<\/span>/gi, (nestedMatch, nestedContent) => {
+                        const nestedStyleMatch = nestedMatch.match(/style="(.*?)"/);
+                        const isNestedBold = isBoldFromStyle(nestedStyleMatch ? nestedStyleMatch[1] : null);
+                        return updateSpacesAndWrapWithAsterisksIfBold(nestedContent, isNestedBold);
+                    });
+
+                    return updateSpacesAndWrapWithAsterisksIfBold(processedInnerContent, isBold);
                 },
             },
             {