diff --git a/src/middlewared/middlewared/job.py b/src/middlewared/middlewared/job.py
index c1e40a1158cf9..04acec90200ab 100644
--- a/src/middlewared/middlewared/job.py
+++ b/src/middlewared/middlewared/job.py
@@ -406,14 +406,14 @@ def set_progress(self, percent=None, description=None, extra=None):
         for wrapped in self.wrapped:
             wrapped.set_progress(**self.progress)
 
-    async def wait(self, timeout=None, raise_error=False):
+    async def wait(self, timeout=None, raise_error=False, raise_error_forward_classes=(CallError,)):
         if timeout is None:
             await self._finished.wait()
         else:
             await asyncio.wait_for(self.middleware.create_task(self._finished.wait()), timeout)
         if raise_error:
             if self.error:
-                if isinstance(self.exc_info[1], CallError):
+                if isinstance(self.exc_info[1], raise_error_forward_classes):
                     raise self.exc_info[1]
 
                 raise CallError(self.error)
diff --git a/src/middlewared/middlewared/plugins/pool_/pool_disk_operations.py b/src/middlewared/middlewared/plugins/pool_/pool_disk_operations.py
index cf700cde170b4..0246f3a5a4b45 100644
--- a/src/middlewared/middlewared/plugins/pool_/pool_disk_operations.py
+++ b/src/middlewared/middlewared/plugins/pool_/pool_disk_operations.py
@@ -1,3 +1,7 @@
+import asyncio
+import errno
+import itertools
+
 from middlewared.schema import accepts, Bool, Dict, Int, returns, Str
 from middlewared.service import CallError, item_method, job, Service, ValidationErrors
 
@@ -181,7 +185,7 @@ async def remove(self, job, oid, options):
         job.set_progress(20, f'Initiating removal of {options["label"]!r} ZFS device')
         await self.middleware.call('zfs.pool.remove', pool['name'], found[1]['guid'])
         job.set_progress(40, 'Waiting for removal of ZFS device to complete')
-        # We would like to wait not for the removal to actually complete for cases where the removal might not
+        # We would like to wait for the removal to actually complete for cases where the removal might not
         # be synchronous like removing top level vdevs except for slog and l2arc
         await self.middleware.call('zfs.pool.wait', pool['name'], {'activity_type': 'REMOVE'})
         job.set_progress(60, 'Removal of ZFS device complete')
@@ -191,24 +195,44 @@ async def remove(self, job, oid, options):
         else:
             disk_paths = [found[1]['path']]
 
-        wipe_jobs = []
+        job.set_progress(70, 'Wiping disks')
+        disks_to_wipe = set()
         for disk_path in disk_paths:
             disk = await self.middleware.call(
                 'disk.label_to_disk', disk_path.replace('/dev/', '')
             )
             if disk:
+                disks_to_wipe.add(disk)
+
+        max_retries = 30
+        disks_errors = {}
+        for retry in itertools.count(1):
+            wipe_jobs = []
+            for disk in disks_to_wipe:
                 wipe_job = await self.middleware.call('disk.wipe', disk, 'QUICK', False)
                 wipe_jobs.append((disk, wipe_job))
 
-        job.set_progress(70, 'Wiping disks')
-        error_str = ''
-        for index, item in enumerate(wipe_jobs):
-            disk, wipe_job = item
-            await wipe_job.wait()
-            if wipe_job.error:
-                error_str += f'{index + 1}) {disk}: {wipe_job.error}\n'
-
-        if error_str:
-            raise CallError(f'Failed to wipe disks:\n{error_str}')
+            disks_errors = {}
+            for disk, wipe_job in wipe_jobs:
+                try:
+                    await wipe_job.wait(raise_error=True, raise_error_forward_classes=(OSError,))
+                except OSError as e:
+                    if not (e.errno == errno.EBUSY and retry < max_retries):
+                        # Sometimes we get this error even after `zfs.pool.wait` confirms the successful device removal
+                        raise
+                except Exception as e:
+                    disks_errors[disk] = str(e)
+                    disks_to_wipe.remove(disk)
+                else:
+                    disks_to_wipe.remove(disk)
+
+            if not disks_to_wipe or disks_errors:
+                break
+
+            await asyncio.sleep(1)
+
+        if disks_errors:
+            disks_errors = '\n'.join(sorted({f'{disk}: {error}' for disk, error in disks_errors.items()}))
+            raise CallError(f'Failed to wipe disks:\n{disks_errors}')
 
         job.set_progress(100, 'Successfully completed wiping disks')
diff --git a/tests/api2/test_pool_remove_disk.py b/tests/api2/test_pool_remove_disk.py
index e61f2b0c62014..38ca637054d9a 100644
--- a/tests/api2/test_pool_remove_disk.py
+++ b/tests/api2/test_pool_remove_disk.py
@@ -1,5 +1,3 @@
-import pytest
-
 from middlewared.test.integration.assets.pool import another_pool
 from middlewared.test.integration.utils import call, ssh