diff --git a/changelog.d/10129.bugfix b/changelog.d/10129.bugfix
new file mode 100644
index 000000000..292676ec8
--- /dev/null
+++ b/changelog.d/10129.bugfix
@@ -0,0 +1 @@
+Add some clarification to the sample config file. Contributed by @Kentokamoto.
diff --git a/docs/sample_config.yaml b/docs/sample_config.yaml
index a2efc1410..16843dd8c 100644
--- a/docs/sample_config.yaml
+++ b/docs/sample_config.yaml
@@ -210,6 +210,8 @@ presence:
 #
 # This option replaces federation_ip_range_blacklist in Synapse v1.25.0.
 #
+# Note: The value is ignored when an HTTP proxy is in use
+#
 #ip_range_blacklist:
 #  - '127.0.0.0/8'
 #  - '10.0.0.0/8'
@@ -972,6 +974,8 @@ media_store_path: "DATADIR/media_store"
 # This must be specified if url_preview_enabled is set. It is recommended that
 # you uncomment the following list as a starting point.
 #
+# Note: The value is ignored when an HTTP proxy is in use
+#
 #url_preview_ip_range_blacklist:
 #  - '127.0.0.0/8'
 #  - '10.0.0.0/8'
diff --git a/synapse/config/repository.py b/synapse/config/repository.py
index 0dfb3a227..7481f3bf5 100644
--- a/synapse/config/repository.py
+++ b/synapse/config/repository.py
@@ -12,9 +12,11 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
+import logging
 import os
 from collections import namedtuple
 from typing import Dict, List
+from urllib.request import getproxies_environment  # type: ignore
 
 from synapse.config.server import DEFAULT_IP_RANGE_BLACKLIST, generate_ip_set
 from synapse.python_dependencies import DependencyException, check_requirements
@@ -22,6 +24,8 @@ from synapse.util.module_loader import load_module
 
 from ._base import Config, ConfigError
 
+logger = logging.getLogger(__name__)
+
 DEFAULT_THUMBNAIL_SIZES = [
     {"width": 32, "height": 32, "method": "crop"},
     {"width": 96, "height": 96, "method": "crop"},
@@ -36,6 +40,9 @@ THUMBNAIL_SIZE_YAML = """\
         #    method: %(method)s
 """
 
+HTTP_PROXY_SET_WARNING = """\
+The Synapse config url_preview_ip_range_blacklist will be ignored as an HTTP(s) proxy is configured."""
+
 ThumbnailRequirement = namedtuple(
     "ThumbnailRequirement", ["width", "height", "method", "media_type"]
 )
@@ -180,12 +187,17 @@ class ContentRepositoryConfig(Config):
                     e.message  # noqa: B306, DependencyException.message is a property
                 )
 
+            proxy_env = getproxies_environment()
             if "url_preview_ip_range_blacklist" not in config:
-                raise ConfigError(
-                    "For security, you must specify an explicit target IP address "
-                    "blacklist in url_preview_ip_range_blacklist for url previewing "
-                    "to work"
-                )
+                if "http" not in proxy_env or "https" not in proxy_env:
+                    raise ConfigError(
+                        "For security, you must specify an explicit target IP address "
+                        "blacklist in url_preview_ip_range_blacklist for url previewing "
+                        "to work"
+                    )
+            else:
+                if "http" in proxy_env or "https" in proxy_env:
+                    logger.warning("".join(HTTP_PROXY_SET_WARNING))
 
             # we always blacklist '0.0.0.0' and '::', which are supposed to be
             # unroutable addresses.
@@ -292,6 +304,8 @@ class ContentRepositoryConfig(Config):
         # This must be specified if url_preview_enabled is set. It is recommended that
         # you uncomment the following list as a starting point.
         #
+        # Note: The value is ignored when an HTTP proxy is in use
+        #
         #url_preview_ip_range_blacklist:
 %(ip_range_blacklist)s
 
diff --git a/synapse/config/server.py b/synapse/config/server.py
index b9e0c0b30..187b4301a 100644
--- a/synapse/config/server.py
+++ b/synapse/config/server.py
@@ -960,6 +960,8 @@ class ServerConfig(Config):
         #
         # This option replaces federation_ip_range_blacklist in Synapse v1.25.0.
         #
+        # Note: The value is ignored when an HTTP proxy is in use
+        #
         #ip_range_blacklist:
 %(ip_range_blacklist)s