diff --git a/src/askui/models/askui/google_genai_api.py b/src/askui/models/askui/google_genai_api.py
index f932bcb0..49b72d03 100644
--- a/src/askui/models/askui/google_genai_api.py
+++ b/src/askui/models/askui/google_genai_api.py
@@ -5,7 +5,14 @@
 from google.genai import types as genai_types
 from google.genai.errors import APIError
 from pydantic import ValidationError
-from tenacity import retry, retry_if_exception, stop_after_attempt, wait_exponential
+from tenacity import (
+    RetryCallState,
+    retry,
+    retry_if_exception,
+    stop_after_attempt,
+    wait_exponential,
+)
+from tenacity.wait import wait_base
 from typing_extensions import override
 
 from askui.logger import logger
@@ -14,12 +21,52 @@
 from askui.models.models import GetModel, ModelName
 from askui.models.shared.prompts import SYSTEM_PROMPT_GET
 from askui.models.types.response_schemas import ResponseSchema, to_response_schema
+from askui.utils.http_utils import parse_retry_after_header
 from askui.utils.image_utils import ImageSource
 
 ASKUI_MODEL_CHOICE_PREFIX = "askui/"
 ASKUI_MODEL_CHOICE_PREFIX_LEN = len(ASKUI_MODEL_CHOICE_PREFIX)
 
 
+class _wait_for_retry_after_header(wait_base):
+    """Wait strategy that tries to wait for the length specified by
+    the Retry-After header, or the underlying wait strategy if not.
+    See RFC 6585 § 4.
+
+    Otherwise, wait according to the fallback strategy.
+    """
+
+    def __init__(self, fallback: wait_base) -> None:
+        """Initialize the wait strategy with a fallback strategy.
+
+        Args:
+            fallback (wait_base): The fallback wait strategy to use when
+                Retry-After header is not available or invalid.
+        """
+        self._fallback = fallback
+
+    def __call__(self, retry_state: RetryCallState) -> float:
+        """Calculate the wait time based on Retry-After header or fallback.
+
+        Args:
+            retry_state (RetryCallState): The retry state containing the
+                exception information.
+
+        Returns:
+            float: The wait time in seconds.
+        """
+        if outcome := retry_state.outcome:
+            exc = outcome.exception()
+            if isinstance(exc, APIError):
+                retry_after: str | None = exc.response.headers.get("Retry-After")
+                if retry_after:
+                    try:
+                        return parse_retry_after_header(retry_after)
+                    except ValueError:
+                        pass
+        return self._fallback(retry_state)
+
+
 def _is_retryable_error(exception: BaseException) -> bool:
     """Check if the exception is a retryable error (status codes 429, 502, or 529).
 
@@ -27,7 +74,7 @@ def _is_retryable_error(exception: BaseException) -> bool:
     retry it.
     """
     if isinstance(exception, APIError):
-        return exception.code in (429, 502, 529)
+        return exception.code in (408, 413, 429, 500, 502, 503, 504, 521, 522, 524)
     return False
 
 
@@ -55,7 +102,9 @@ def __init__(self, settings: AskUiInferenceApiSettings | None = None) -> None:
 
     @retry(
         stop=stop_after_attempt(4),  # 3 retries
-        wait=wait_exponential(multiplier=30, min=30, max=120),  # 30s, 60s, 120s
+        wait=_wait_for_retry_after_header(
+            wait_exponential(multiplier=30, min=30, max=120)
+        ),  # retry after or as a fallback 30s, 60s, 120s
         retry=retry_if_exception(_is_retryable_error),
         reraise=True,
     )
diff --git a/src/askui/utils/http_utils.py b/src/askui/utils/http_utils.py
new file mode 100644
index 00000000..3969ce2f
--- /dev/null
+++ b/src/askui/utils/http_utils.py
@@ -0,0 +1,36 @@
+from datetime import datetime, timezone
+
+
+def parse_retry_after_header(retry_after: str) -> float:
+    """Parse the Retry-After header value.
+
+    The Retry-After header value can be a number of seconds or a date in
+    RFC 2822 format:
+    - `<number>`
+    - `<day-name>, <day> <month> <year> <hour>:<minute>:<second> GMT`
+
+    The date must be in GMT timezone.
+
+    Args:
+        retry_after (str): The Retry-After header value.
+
+    Returns:
+        float: The number of seconds to wait.
+
+    Raises:
+        ValueError: If the header value cannot be parsed.
+    """
+    try:
+        return float(retry_after)
+    except (TypeError, ValueError):
+        try:
+            dt = datetime.strptime(  # noqa: DTZ007
+                retry_after,
+                "%a, %d %b %Y %H:%M:%S GMT",
+            )
+            dt = dt.replace(tzinfo=timezone.utc)
+            now = datetime.now(timezone.utc)
+            return (dt - now).total_seconds()
+        except (TypeError, ValueError) as e:
+            error_msg = f"Could not parse Retry-After header: {retry_after}"
+            raise ValueError(error_msg) from e
diff --git a/tests/unit/utils/test_http_utils.py b/tests/unit/utils/test_http_utils.py
new file mode 100644
index 00000000..03c895b3
--- /dev/null
+++ b/tests/unit/utils/test_http_utils.py
@@ -0,0 +1,145 @@
+from datetime import datetime, timezone
+from unittest.mock import patch
+
+import pytest
+
+from askui.utils.http_utils import parse_retry_after_header
+
+
+class TestParseRetryAfterHeader:
+    """Test cases for the `parse_retry_after_header` function."""
+
+    def test_parse_numeric_seconds(self) -> None:
+        """Test parsing numeric retry-after values."""
+        assert parse_retry_after_header("30") == 30.0
+        assert parse_retry_after_header("60.5") == 60.5
+        assert parse_retry_after_header("0") == 0.0
+        assert parse_retry_after_header("120") == 120.0
+
+    def test_parse_rfc2822_date_format(self) -> None:
+        """Test parsing RFC 2822 date format retry-after values."""
+        # Test with a future date
+        future_date = "Mon, 15 Jan 2024 12:00:00 GMT"
+        with patch("askui.utils.http_utils.datetime") as mock_datetime:
+            # Mock current time to be before the retry-after date
+            mock_datetime.now.return_value = datetime(
+                2024, 1, 15, 11, 0, 0, tzinfo=timezone.utc
+            )
+            mock_datetime.strptime = datetime.strptime
+
+            result = parse_retry_after_header(future_date)
+            assert result > 0  # Should be positive seconds
+
+    def test_parse_rfc2822_date_format_past_date(self) -> None:
+        """Test parsing RFC 2822 date format with past date."""
+        past_date = "Mon, 15 Jan 2024 10:00:00 GMT"
+        with patch("askui.utils.http_utils.datetime") as mock_datetime:
+            # Mock current time to be after the retry-after date
+            mock_datetime.now.return_value = datetime(
+                2024, 1, 15, 11, 0, 0, tzinfo=timezone.utc
+            )
+            mock_datetime.strptime = datetime.strptime
+
+            result = parse_retry_after_header(past_date)
+            assert result < 0  # Should be negative seconds (past date)
+
+    def test_parse_rfc2822_date_format_exact_time(self) -> None:
+        """Test parsing RFC 2822 date format with exact current time."""
+        exact_date = "Mon, 15 Jan 2024 11:00:00 GMT"
+        with patch("askui.utils.http_utils.datetime") as mock_datetime:
+            # Mock current time to be exactly the retry-after date
+            mock_datetime.now.return_value = datetime(
+                2024, 1, 15, 11, 0, 0, tzinfo=timezone.utc
+            )
+            mock_datetime.strptime = datetime.strptime
+
+            result = parse_retry_after_header(exact_date)
+            assert result == 0.0  # Should be zero seconds
+
+    def test_parse_invalid_numeric_input(self) -> None:
+        """Test parsing invalid numeric inputs."""
+        with pytest.raises(
+            ValueError, match="Could not parse Retry-After header: invalid"
+        ):
+            parse_retry_after_header("invalid")
+
+    def test_parse_invalid_date_format(self) -> None:
+        """Test parsing invalid date format inputs."""
+        with pytest.raises(
+            ValueError, match="Could not parse Retry-After header: invalid_date"
+        ):
+            parse_retry_after_header("invalid_date")
+
+    def test_parse_empty_string(self) -> None:
+        """Test parsing empty string input."""
+        with pytest.raises(ValueError, match="Could not parse Retry-After header: "):
+            parse_retry_after_header("")
+
+    def test_parse_whitespace_string(self) -> None:
+        """Test parsing whitespace-only string input."""
+        with pytest.raises(ValueError, match="Could not parse Retry-After header:    "):
+            parse_retry_after_header("   ")
+
+    def test_parse_none_input(self) -> None:
+        """Test parsing None input."""
+        with pytest.raises(
+            ValueError, match="Could not parse Retry-After header: None"
+        ):
+            parse_retry_after_header(None)  # type: ignore
+
+    def test_parse_malformed_date(self) -> None:
+        """Test parsing malformed date string."""
+        malformed_date = "Mon, 15 Jan 2024 25:00:00 GMT"  # Invalid hour
+        with pytest.raises(
+            ValueError,
+            match="Could not parse Retry-After header: Mon, 15 Jan 2024 25:00:00 GMT",
+        ):
+            parse_retry_after_header(malformed_date)
+
+    def test_parse_date_without_gmt(self) -> None:
+        """Test parsing date without GMT timezone."""
+        date_without_gmt = "Mon, 15 Jan 2024 12:00:00"
+        with pytest.raises(
+            ValueError,
+            match="Could not parse Retry-After header: Mon, 15 Jan 2024 12:00:00",
+        ):
+            parse_retry_after_header(date_without_gmt)
+
+    def test_parse_negative_numeric(self) -> None:
+        """Test parsing negative numeric values."""
+        assert parse_retry_after_header("-30") == -30.0
+        assert parse_retry_after_header("-60.5") == -60.5
+
+    def test_parse_large_numeric(self) -> None:
+        """Test parsing large numeric values."""
+        assert parse_retry_after_header("86400") == 86400.0  # 24 hours
+        assert parse_retry_after_header("31536000") == 31536000.0  # 1 year
+
+    def test_parse_scientific_notation(self) -> None:
+        """Test parsing scientific notation."""
+        assert parse_retry_after_header("1e3") == 1000.0
+        assert parse_retry_after_header("1.5e2") == 150.0
+
+    def test_parse_edge_case_dates(self) -> None:
+        """Test parsing edge case date formats."""
+        # Test leap year date
+        leap_year_date = "Mon, 29 Feb 2024 12:00:00 GMT"
+        with patch("askui.utils.http_utils.datetime") as mock_datetime:
+            mock_datetime.now.return_value = datetime(
+                2024, 2, 29, 11, 0, 0, tzinfo=timezone.utc
+            )
+            mock_datetime.strptime = datetime.strptime
+
+            result = parse_retry_after_header(leap_year_date)
+            assert result > 0
+
+        # Test end of year date
+        end_year_date = "Mon, 31 Dec 2024 23:59:59 GMT"
+        with patch("askui.utils.http_utils.datetime") as mock_datetime:
+            mock_datetime.now.return_value = datetime(
+                2024, 12, 31, 23, 0, 0, tzinfo=timezone.utc
+            )
+            mock_datetime.strptime = datetime.strptime
+
+            result = parse_retry_after_header(end_year_date)
+            assert result > 0