diff --git a/packages/text-markdown/src/__tests__/markdown.test.ts b/packages/text-markdown/src/__tests__/markdown.test.ts
index 4ecdf49731..221bf004c1 100644
--- a/packages/text-markdown/src/__tests__/markdown.test.ts
+++ b/packages/text-markdown/src/__tests__/markdown.test.ts
@@ -13,6 +13,7 @@
 // limitations under the License.
 //
 
+import { MarkupNode } from '@hcengineering/text-core'
 import { markdownToMarkup, markupToMarkdown } from '..'
 import { isMarkdownsEquals } from '../compare'
 
@@ -855,8 +856,65 @@ Lorem ipsum dolor sit amet.
   })
 })
 
+describe('markupToMarkdown', () => {
+  const tests: Array<{ name: string, markdown: string, markup: object }> = [
+    {
+      name: 'links',
+      markdown: `[Link](https://example.com)
+
+[Link with spaces](<https://example.com/with spaces>)
+
+[Link with spaces and braces](<https://example.com/\\<with spaces\\>>)`,
+      markup: {
+        type: 'doc',
+        content: [
+          {
+            type: 'paragraph',
+            content: [
+              {
+                type: 'text',
+                text: 'Link',
+                marks: [{ type: 'link', attrs: { href: 'https://example.com' } }]
+              }
+            ]
+          },
+          {
+            type: 'paragraph',
+            content: [
+              {
+                type: 'text',
+                text: 'Link with spaces',
+                marks: [{ type: 'link', attrs: { href: 'https://example.com/with spaces' } }]
+              }
+            ]
+          },
+          {
+            type: 'paragraph',
+            content: [
+              {
+                type: 'text',
+                text: 'Link with spaces and braces',
+                marks: [{ type: 'link', attrs: { href: 'https://example.com/<with spaces>' } }]
+              }
+            ]
+          }
+        ]
+      }
+    }
+  ]
+
+  describe('to markdown', () => {
+    tests.forEach(({ name, markdown, markup }) => {
+      it(name, () => {
+        const result = markupToMarkdown(markup as MarkupNode, options)
+        expect(result).toEqual(markdown)
+      })
+    })
+  })
+})
+
 describe('markdownToMarkup -> markupToMarkdown', () => {
-  const tests: Array<{ name: string, markdown: string }> = [
+  const tests: Array<{ name: string, markdown: string, alternate?: string }> = [
     { name: 'Italic', markdown: '*Asteriscs* and _Underscores_' },
     { name: 'Bold', markdown: '**Asteriscs** and __Underscores__' },
     { name: 'Bullet list with asteriscs', markdown: 'Asterisks :\r\n* Firstly\r\n* Secondly' },
@@ -878,6 +936,16 @@ describe('markdownToMarkup -> markupToMarkdown', () => {
       name: 'Link',
       markdown: 'See [link](https://example.com)'
     },
+    {
+      name: 'Link with spaces',
+      markdown: 'See [link](<https://example.com/with spaces>)',
+      alternate: 'See [link](https://example.com/with%20spaces)'
+    },
+    {
+      name: 'Link with spaces and braces',
+      markdown: 'See [link](<https://example.com/\\<with spaces\\>>)',
+      alternate: 'See [link](https://example.com/%3Cwith%20spaces%3E)'
+    },
     {
       name: 'Codeblock',
       markdown: '```typescript\nconst x: number = 42;\n```'
@@ -901,11 +969,11 @@ describe('markdownToMarkup -> markupToMarkdown', () => {
     // }
   ]
 
-  tests.forEach(({ name, markdown }) => {
+  tests.forEach(({ name, markdown, alternate }) => {
     it(name, () => {
       const json = markdownToMarkup(markdown, options)
       const serialized = markupToMarkdown(json, options)
-      expect(serialized).toEqualMarkdown(markdown)
+      expect(serialized).toEqualMarkdown(alternate ?? markdown)
     })
   })
 })
diff --git a/packages/text-markdown/src/serializer.ts b/packages/text-markdown/src/serializer.ts
index d0a46022b2..53270e578d 100644
--- a/packages/text-markdown/src/serializer.ts
+++ b/packages/text-markdown/src/serializer.ts
@@ -351,11 +351,16 @@ export const storeMarks: Record<string, MarkProcessor> = {
       } else {
         const { inAutolink } = state
         state.inAutolink = undefined
+
+        const href = (mark.attrs?.href as string) ?? ''
+        // eslint-disable-next-line
+        const url = href.replace(/[\(\)"\\<>]/g, '\\$&')
+        const hasSpaces = url.includes(' ')
+
         return inAutolink === true
           ? '>'
           : '](' +
-              // eslint-disable-next-line
-              (mark.attrs?.href as string).replace(/[\(\)"]/g, '\\$&') +
+              (hasSpaces ? `<${url}>` : url) +
               (mark.attrs?.title !== undefined ? ` "${(mark.attrs?.title as string).replace(/"/g, '\\"')}"` : '') +
               ')'
       }