diff --git a/README.md b/README.md
index 634cff5a5..7b8f3f669 100644
--- a/README.md
+++ b/README.md
@@ -352,9 +352,13 @@ ## General Options:
                                     (Experimental)
     --no-live-from-start            Download livestreams from the current time
                                     (default)
-    --wait-for-video MIN[-MAX]      Wait for scheduled streams to become
+    --wait-for-video MIN[-MAX][:RETRIES]
+                                    Wait for scheduled streams to become
                                     available. Pass the minimum number of
-                                    seconds (or range) to wait between retries
+                                    seconds (or range) to wait between retries.
+                                    RETRIES is the maximum number of additional
+                                    attempts if the video is still unavailable
+                                    after waiting (default is infinite)
     --no-wait-for-video             Do not wait for scheduled streams (default)
     --mark-watched                  Mark videos watched (even with --simulate)
     --no-mark-watched               Do not mark videos watched (default)
diff --git a/yt_dlp/YoutubeDL.py b/yt_dlp/YoutubeDL.py
index 8790b326b..b207b98c9 100644
--- a/yt_dlp/YoutubeDL.py
+++ b/yt_dlp/YoutubeDL.py
@@ -105,6 +105,7 @@
     Popen,
     PostProcessingError,
     ReExtractInfo,
+    ReExtractInfoLater,
     RejectedVideoReached,
     SameFileError,
     UnavailableVideoError,
@@ -1646,11 +1647,27 @@ def extract_info(self, url, download=True, ie_key=None, extra_info=None,
     def _handle_extraction_exceptions(func):
         @functools.wraps(func)
         def wrapper(self, *args, **kwargs):
+            wait_retries = 0
+            wait_range = self.params.get('wait_for_video')
+            max_retries = float('inf')
+            if wait_range and wait_range[2] is not None:
+                max_retries = wait_range[2]
             while True:
                 try:
                     return func(self, *args, **kwargs)
                 except (CookieLoadError, DownloadCancelled, LazyList.IndexError, PagedList.IndexError):
                     raise
+                except ReExtractInfoLater as e:
+                    if wait_retries > max_retries:
+                        if max_retries > 0:
+                            self.report_error(f'[wait] Giving up after {wait_retries - 1} {"retries" if wait_retries != 2 else "retry"} while waiting.')
+                        else:
+                            self.report_error('[wait] Video is still unavailable after waiting.')
+                        return
+                    self._wait_until(e.time)
+                    wait_retries += 1
+                    self.to_screen('[wait] Re-extracting data')
+                    continue
                 except ReExtractInfo as e:
                     if e.expected:
                         self.to_screen(f'{e}; Re-extracting data')
@@ -1675,12 +1692,7 @@ def wrapper(self, *args, **kwargs):
                 break
         return wrapper
 
-    def _wait_for_video(self, ie_result={}):
-        if (not self.params.get('wait_for_video')
-                or ie_result.get('_type', 'video') != 'video'
-                or ie_result.get('formats') or ie_result.get('url')):
-            return
-
+    def _wait_until(self, till):
         format_dur = lambda dur: '%02d:%02d:%02d' % timetuple_from_msec(dur * 1000)[:-1]
         last_msg = ''
 
@@ -1694,7 +1706,31 @@ def progress(msg):
             self.to_screen(full_msg, skip_eol=True)
             last_msg = msg
 
-        min_wait, max_wait = self.params.get('wait_for_video')
+        diff = till - time.time()
+        self.to_screen(f'[wait] Waiting for {format_dur(diff)} - Press Ctrl+C to interrupt')
+        try:
+            while True:
+                diff = till - time.time()
+                if diff <= 0:
+                    progress('')
+                    self.to_screen('[wait] Wait period ended')
+                    return
+                progress(f'[wait] Remaining time until next attempt: {self._format_screen(format_dur(diff), self.Styles.EMPHASIS)}')
+                time.sleep(1)
+        except KeyboardInterrupt:
+            progress('')
+            self.to_screen('[wait] Interrupted by user')
+        except BaseException:
+            self.to_screen('')
+            raise
+
+    def _wait_for_video(self, ie_result={}):
+        if (not self.params.get('wait_for_video')
+                or ie_result.get('_type', 'video') != 'video'
+                or ie_result.get('formats') or ie_result.get('url')):
+            return
+
+        min_wait, max_wait, _ = self.params.get('wait_for_video')
         diff = try_get(ie_result, lambda x: x['release_timestamp'] - time.time())
         if diff is None and ie_result.get('live_status') == 'is_upcoming':
             diff = round(random.uniform(min_wait, max_wait) if (max_wait and min_wait) else (max_wait or min_wait), 0)
@@ -1702,24 +1738,7 @@ def progress(msg):
         elif ie_result and (diff or 0) <= 0:
             self.report_warning('Video should already be available according to extracted info')
         diff = min(max(diff or 0, min_wait or 0), max_wait or float('inf'))
-        self.to_screen(f'[wait] Waiting for {format_dur(diff)} - Press Ctrl+C to try now')
-
-        wait_till = time.time() + diff
-        try:
-            while True:
-                diff = wait_till - time.time()
-                if diff <= 0:
-                    progress('')
-                    raise ReExtractInfo('[wait] Wait period ended', expected=True)
-                progress(f'[wait] Remaining time until next attempt: {self._format_screen(format_dur(diff), self.Styles.EMPHASIS)}')
-                time.sleep(1)
-        except KeyboardInterrupt:
-            progress('')
-            raise ReExtractInfo('[wait] Interrupted by user', expected=True)
-        except BaseException as e:
-            if not isinstance(e, ReExtractInfo):
-                self.to_screen('')
-            raise
+        raise ReExtractInfoLater(time.time() + diff)
 
     def _load_cookies(self, data, *, autoscope=True):
         """Loads cookies from a `Cookie` header
diff --git a/yt_dlp/__init__.py b/yt_dlp/__init__.py
index 7d8f10047..6998949fa 100644
--- a/yt_dlp/__init__.py
+++ b/yt_dlp/__init__.py
@@ -224,12 +224,37 @@ def validate_minmax(min_val, max_val, min_name, max_name=None):
     else:
         validate_minmax(opts.sleep_interval, opts.max_sleep_interval, 'sleep interval')
 
+    def parse_retries(name, value):
+        if value is None:
+            return None
+        elif value in ('inf', 'infinite'):
+            return float('inf')
+        try:
+            int_value = int(value)
+        except (TypeError, ValueError):
+            validate(False, f'{name} retry count', value)
+        validate_positive(f'{name} retry count', int_value)
+        return int_value
+
+    def parse_range_with_arg(name, arg_name, value,
+                             parse_limits=parse_duration, parse_arg=parse_retries):
+        # syntax: MIN[-MAX][:N]
+        m = re.fullmatch(r'([^-:]+)(-[^:]+)?(:.+)?', value)
+        validate(m, name, value)
+        min_val, max_val, arg_val = m.groups()
+
+        min_lim, max_lim = map(parse_limits, [min_val, (max_val and max_val[1:])])
+        validate(min_lim is not None, name, value)
+        validate(max_val is None or max_lim is not None, name, value)
+        validate_minmax(min_lim, max_lim, name)
+
+        parsed_arg = parse_arg(arg_name, arg_val and arg_val[1:])
+        return (min_lim, max_lim, parsed_arg)
+
     if opts.wait_for_video is not None:
-        min_wait, max_wait, *_ = map(parse_duration, [*opts.wait_for_video.split('-', 1), None])
-        validate(min_wait is not None and not (max_wait is None and '-' in opts.wait_for_video),
-                 'time range to wait for video', opts.wait_for_video)
-        validate_minmax(min_wait, max_wait, 'time range to wait for video')
-        opts.wait_for_video = (min_wait, max_wait)
+        min_wait, max_wait, wait_retries = parse_range_with_arg(
+            'time range to wait for video', 'waiting', opts.wait_for_video)
+        opts.wait_for_video = (min_wait, max_wait, wait_retries)
 
     # Format sort
     for f in opts.format_sort:
@@ -254,18 +279,6 @@ def validate_minmax(min_val, max_val, min_name, max_name=None):
         validate_positive('audio quality', int_or_none(float_or_none(opts.audioquality), default=0))
 
     # Retries
-    def parse_retries(name, value):
-        if value is None:
-            return None
-        elif value in ('inf', 'infinite'):
-            return float('inf')
-        try:
-            int_value = int(value)
-        except (TypeError, ValueError):
-            validate(False, f'{name} retry count', value)
-        validate_positive(f'{name} retry count', int_value)
-        return int_value
-
     opts.retries = parse_retries('download', opts.retries)
     opts.fragment_retries = parse_retries('fragment', opts.fragment_retries)
     opts.extractor_retries = parse_retries('extractor', opts.extractor_retries)
diff --git a/yt_dlp/options.py b/yt_dlp/options.py
index 91c2635a7..f045e99f4 100644
--- a/yt_dlp/options.py
+++ b/yt_dlp/options.py
@@ -445,10 +445,12 @@ def _alias_callback(option, opt_str, value, parser, opts, nargs):
         help='Download livestreams from the current time (default)')
     general.add_option(
         '--wait-for-video',
-        dest='wait_for_video', metavar='MIN[-MAX]', default=None,
+        dest='wait_for_video', metavar='MIN[-MAX][:RETRIES]', default=None,
         help=(
             'Wait for scheduled streams to become available. '
-            'Pass the minimum number of seconds (or range) to wait between retries'))
+            'Pass the minimum number of seconds (or range) to wait between retries. '
+            'RETRIES is the maximum number of additional attempts if the video '
+            'is still unavailable after waiting (default is infinite)'))
     general.add_option(
         '--no-wait-for-video',
         dest='wait_for_video', action='store_const', const=None,
diff --git a/yt_dlp/utils/_utils.py b/yt_dlp/utils/_utils.py
index 4093c238c..9216644a8 100644
--- a/yt_dlp/utils/_utils.py
+++ b/yt_dlp/utils/_utils.py
@@ -1115,6 +1115,15 @@ def __init__(self, msg, expected=False):
         self.expected = expected
 
 
+class ReExtractInfoLater(ReExtractInfo):
+    """ Video info needs to be re-extracted after a waiting period. """
+    msg = 'Video is not available yet'
+
+    def __init__(self, time):
+        super().__init__(self.msg, expected=True)
+        self.time = time
+
+
 class ThrottledDownload(ReExtractInfo):
     """ Download speed below --throttled-rate. """
     msg = 'The download speed is below throttle limit'