diff --git a/doc/API.md b/doc/API.md
index 51084c06..db96bb10 100644
--- a/doc/API.md
+++ b/doc/API.md
@@ -13,6 +13,7 @@
    - [Error handling](#error-handling)
    - [Field selecting](#field-selecting)
    - [Versioning](#versioning)
+   - [Webhooks](#webhooks)
 
 2. [API reference](#api-reference)
 
@@ -276,6 +277,15 @@ reject the request as well, in which case the client is encouraged to notify
 the user about the situation.
 
 
+## Webhooks
+
+System administrators can choose to configure webhooks to track events.
+Webhook URIs can be configured in `config.yaml` (See `config.yaml.dist` for
+example). Upon any event, the API will send a `POST` request to the listed
+URIs with a [snapshot resource](#snapshot) generated with anonymous user
+privileges as the message body, in JSON format.
+
+
 # API reference
 
 Depending on the deployment, the URLs might be relative to some base path such
diff --git a/server/config.yaml.dist b/server/config.yaml.dist
index 937c1387..e3799a35 100644
--- a/server/config.yaml.dist
+++ b/server/config.yaml.dist
@@ -39,8 +39,9 @@ smtp:
     user: # example: bot
     pass: # example: groovy123
     from: # example: noreply@example.com
-    # if host is left empty the password reset feature will be disabled, in which case it is
-    # recommended to fill contactEmail so that users know who to contact when they want to reset their password
+    # if host is left empty the password reset feature will be disabled,
+    # in which case it is recommended to fill contactEmail so that users
+    # know who to contact when they want to reset their password
 
 contact_email: # example: bob@example.com. Meant for manual password reset procedures
 
@@ -58,6 +59,12 @@ pool_category_name_regex: ^[^\s%+#/]+$
 password_regex: '^.{5,}$'
 user_name_regex: '^[a-zA-Z0-9_-]{1,32}$'
 
+# webhooks to call when events occur (such as post/tag/user/etc. changes)
+# the listed urls will be called with a HTTP POST request with a payload
+# containing a snapshot resource as JSON. See doc/API.md for details
+webhooks:
+    # - https://api.example.com/webhooks/
+
 default_rank: regular
 
 privileges:
diff --git a/server/szurubooru/facade.py b/server/szurubooru/facade.py
index f1a9a072..ecf34c74 100644
--- a/server/szurubooru/facade.py
+++ b/server/szurubooru/facade.py
@@ -94,6 +94,11 @@ def validate_config() -> None:
     if not config.config["database"]:
         raise errors.ConfigError("Database is not configured")
 
+    if config.config["webhooks"] and not isinstance(
+        config.config["webhooks"], list
+    ):
+        raise errors.ConfigError("Webhooks must be provided as a list of URLs")
+
     if config.config["smtp"]["host"]:
         if not config.config["smtp"]["port"]:
             raise errors.ConfigError("SMTP host is set but port is not set")
diff --git a/server/szurubooru/func/net.py b/server/szurubooru/func/net.py
index ddac65c8..bb43dddb 100644
--- a/server/szurubooru/func/net.py
+++ b/server/szurubooru/func/net.py
@@ -1,7 +1,10 @@
+import json
 import logging
 import os
+import urllib.error
 import urllib.request
 from tempfile import NamedTemporaryFile
+from typing import Any, Dict, List
 
 from youtube_dl import YoutubeDL
 from youtube_dl.utils import YoutubeDLError
@@ -58,3 +61,24 @@ def _youtube_dl_wrapper(url: str) -> bytes:
         raise errors.ThirdPartyError(
             "Error downloading video %s (file could not be saved)" % (url)
         )
+
+
+def post_to_webhooks(payload: Dict[str, Any]) -> List[int]:
+    return_list = []
+    for webhook in config.config["webhooks"] or []:
+        req = urllib.request.Request(webhook)
+        req.data = json.dumps(
+            payload, default=lambda x: x.isoformat("T") + "Z",
+        ).encode("utf-8")
+        req.add_header("Content-Type", "application/json")
+        try:
+            res = urllib.request.urlopen(req)
+            if not 200 <= res.status <= 299:
+                logger.warning(
+                    f"Webhook {webhook} returned {res.status} {res.reason}"
+                )
+            return_list.append(res.status)
+        except urllib.error.URLError as e:
+            logger.error(f"Unable to call webhook {webhook}: {str(e)}")
+            return_list.append(400)
+    return return_list
diff --git a/server/szurubooru/func/snapshots.py b/server/szurubooru/func/snapshots.py
index b34b7022..afb26ea5 100644
--- a/server/szurubooru/func/snapshots.py
+++ b/server/szurubooru/func/snapshots.py
@@ -4,7 +4,7 @@ from typing import Any, Callable, Dict, Optional
 import sqlalchemy as sa
 
 from szurubooru import db, model
-from szurubooru.func import diff, users
+from szurubooru.func import diff, net, users
 
 
 def get_tag_category_snapshot(category: model.TagCategory) -> Dict[str, Any]:
@@ -93,6 +93,13 @@ def serialize_snapshot(
     }
 
 
+def _post_to_webhooks(snapshot: model.Snapshot) -> None:
+    webhook_user = model.User()
+    webhook_user.name = None
+    webhook_user.rank = "anonymous"
+    net.post_to_webhooks(serialize_snapshot(snapshot, webhook_user))
+
+
 def _create(
     operation: str, entity: model.Base, auth_user: Optional[model.User]
 ) -> model.Snapshot:
@@ -116,6 +123,7 @@ def create(entity: model.Base, auth_user: Optional[model.User]) -> None:
     snapshot_factory = _snapshot_factories[snapshot.resource_type]
     snapshot.data = snapshot_factory(entity)
     db.session.add(snapshot)
+    _post_to_webhooks(snapshot)
 
 
 def modify(entity: model.Base, auth_user: Optional[model.User]) -> None:
@@ -147,6 +155,7 @@ def modify(entity: model.Base, auth_user: Optional[model.User]) -> None:
     if not snapshot.data:
         return
     db.session.add(snapshot)
+    _post_to_webhooks(snapshot)
 
 
 def delete(entity: model.Base, auth_user: Optional[model.User]) -> None:
@@ -155,6 +164,7 @@ def delete(entity: model.Base, auth_user: Optional[model.User]) -> None:
     snapshot_factory = _snapshot_factories[snapshot.resource_type]
     snapshot.data = snapshot_factory(entity)
     db.session.add(snapshot)
+    _post_to_webhooks(snapshot)
 
 
 def merge(
@@ -174,3 +184,4 @@ def merge(
     ) = model.util.get_resource_info(target_entity)
     snapshot.data = [resource_type, resource_name]
     db.session.add(snapshot)
+    _post_to_webhooks(snapshot)
diff --git a/server/szurubooru/tests/api/test_pool_category_updating.py b/server/szurubooru/tests/api/test_pool_category_updating.py
index d934e603..c13112f4 100644
--- a/server/szurubooru/tests/api/test_pool_category_updating.py
+++ b/server/szurubooru/tests/api/test_pool_category_updating.py
@@ -67,7 +67,7 @@ def test_omitting_optional_field(
     del params[field]
     with patch("szurubooru.func.pool_categories.serialize_category"), patch(
         "szurubooru.func.pool_categories.update_category_name"
-    ):
+    ), patch("szurubooru.func.snapshots._post_to_webhooks"):
         api.pool_category_api.update_pool_category(
             context_factory(
                 params={**params, **{"version": 1}},
diff --git a/server/szurubooru/tests/api/test_pool_creating.py b/server/szurubooru/tests/api/test_pool_creating.py
index a9f1473f..4fd89396 100644
--- a/server/szurubooru/tests/api/test_pool_creating.py
+++ b/server/szurubooru/tests/api/test_pool_creating.py
@@ -70,7 +70,7 @@ def test_omitting_optional_field(
     del params[field]
     with patch("szurubooru.func.pools.create_pool"), patch(
         "szurubooru.func.pools.serialize_pool"
-    ):
+    ), patch("szurubooru.func.snapshots._post_to_webhooks"):
         pools.create_pool.return_value = pool_factory()
         api.pool_api.create_pool(
             context_factory(
diff --git a/server/szurubooru/tests/api/test_pool_deleting.py b/server/szurubooru/tests/api/test_pool_deleting.py
index 387aca10..5c5adcc1 100644
--- a/server/szurubooru/tests/api/test_pool_deleting.py
+++ b/server/szurubooru/tests/api/test_pool_deleting.py
@@ -34,17 +34,18 @@ def test_deleting_used(
     pool.posts.append(post)
     db.session.add_all([pool, post])
     db.session.commit()
-    api.pool_api.delete_pool(
-        context_factory(
-            params={"version": 1},
-            user=user_factory(rank=model.User.RANK_REGULAR),
-        ),
-        {"pool_id": 1},
-    )
-    db.session.refresh(post)
-    assert db.session.query(model.Pool).count() == 0
-    assert db.session.query(model.PoolPost).count() == 0
-    assert post.pools == []
+    with patch("szurubooru.func.snapshots._post_to_webhooks"):
+        api.pool_api.delete_pool(
+            context_factory(
+                params={"version": 1},
+                user=user_factory(rank=model.User.RANK_REGULAR),
+            ),
+            {"pool_id": 1},
+        )
+        db.session.refresh(post)
+        assert db.session.query(model.Pool).count() == 0
+        assert db.session.query(model.PoolPost).count() == 0
+        assert post.pools == []
 
 
 def test_trying_to_delete_non_existing(user_factory, context_factory):
diff --git a/server/szurubooru/tests/api/test_post_creating.py b/server/szurubooru/tests/api/test_post_creating.py
index 4e05cf11..e2db0eba 100644
--- a/server/szurubooru/tests/api/test_post_creating.py
+++ b/server/szurubooru/tests/api/test_post_creating.py
@@ -143,7 +143,9 @@ def test_anonymous_uploads(
 
     with patch("szurubooru.func.posts.serialize_post"), patch(
         "szurubooru.func.posts.create_post"
-    ), patch("szurubooru.func.posts.update_post_source"):
+    ), patch("szurubooru.func.posts.update_post_source"), patch(
+        "szurubooru.func.snapshots._post_to_webhooks"
+    ):
         config_injector(
             {
                 "privileges": {
@@ -181,6 +183,8 @@ def test_creating_from_url_saves_source(
         "szurubooru.func.posts.serialize_post"
     ), patch("szurubooru.func.posts.create_post"), patch(
         "szurubooru.func.posts.update_post_source"
+    ), patch(
+        "szurubooru.func.snapshots._post_to_webhooks"
     ):
         config_injector(
             {
@@ -223,6 +227,8 @@ def test_creating_from_url_with_source_specified(
         "szurubooru.func.posts.serialize_post"
     ), patch("szurubooru.func.posts.create_post"), patch(
         "szurubooru.func.posts.update_post_source"
+    ), patch(
+        "szurubooru.func.snapshots._post_to_webhooks"
     ):
         config_injector(
             {
@@ -334,7 +340,7 @@ def test_errors_not_spending_ids(
     # successful request
     with patch("szurubooru.func.posts.serialize_post"), patch(
         "szurubooru.func.posts.update_post_tags"
-    ):
+    ), patch("szurubooru.func.snapshots._post_to_webhooks"):
         posts.serialize_post.side_effect = lambda post, *_, **__: post.post_id
         post1_id = api.post_api.create_post(
             context_factory(
@@ -357,7 +363,7 @@ def test_errors_not_spending_ids(
     # successful request
     with patch("szurubooru.func.posts.serialize_post"), patch(
         "szurubooru.func.posts.update_post_tags"
-    ):
+    ), patch("szurubooru.func.snapshots._post_to_webhooks"):
         posts.serialize_post.side_effect = lambda post, *_, **__: post.post_id
         post2_id = api.post_api.create_post(
             context_factory(
diff --git a/server/szurubooru/tests/api/test_post_featuring.py b/server/szurubooru/tests/api/test_post_featuring.py
index e1f8cef8..d83d4b6b 100644
--- a/server/szurubooru/tests/api/test_post_featuring.py
+++ b/server/szurubooru/tests/api/test_post_featuring.py
@@ -55,7 +55,9 @@ def test_trying_to_feature_the_same_post_twice(
 ):
     db.session.add(post_factory(id=1))
     db.session.commit()
-    with patch("szurubooru.func.posts.serialize_post"):
+    with patch("szurubooru.func.posts.serialize_post"), patch(
+        "szurubooru.func.snapshots._post_to_webhooks"
+    ):
         api.post_api.set_featured_post(
             context_factory(
                 params={"id": 1},
@@ -80,7 +82,9 @@ def test_featuring_one_post_after_another(
     assert posts.try_get_featured_post() is None
     assert not posts.get_post_by_id(1).is_featured
     assert not posts.get_post_by_id(2).is_featured
-    with patch("szurubooru.func.posts.serialize_post"):
+    with patch("szurubooru.func.posts.serialize_post"), patch(
+        "szurubooru.func.snapshots._post_to_webhooks"
+    ):
         with fake_datetime("1997"):
             api.post_api.set_featured_post(
                 context_factory(
diff --git a/server/szurubooru/tests/api/test_tag_category_updating.py b/server/szurubooru/tests/api/test_tag_category_updating.py
index 0d593900..6c32737b 100644
--- a/server/szurubooru/tests/api/test_tag_category_updating.py
+++ b/server/szurubooru/tests/api/test_tag_category_updating.py
@@ -65,7 +65,7 @@ def test_omitting_optional_field(
     del params[field]
     with patch("szurubooru.func.tag_categories.serialize_category"), patch(
         "szurubooru.func.tag_categories.update_category_name"
-    ):
+    ), patch("szurubooru.func.snapshots._post_to_webhooks"):
         api.tag_category_api.update_tag_category(
             context_factory(
                 params={**params, **{"version": 1}},
diff --git a/server/szurubooru/tests/api/test_tag_creating.py b/server/szurubooru/tests/api/test_tag_creating.py
index 648b3178..2f4264db 100644
--- a/server/szurubooru/tests/api/test_tag_creating.py
+++ b/server/szurubooru/tests/api/test_tag_creating.py
@@ -71,7 +71,7 @@ def test_omitting_optional_field(
     del params[field]
     with patch("szurubooru.func.tags.create_tag"), patch(
         "szurubooru.func.tags.serialize_tag"
-    ):
+    ), patch("szurubooru.func.snapshots._post_to_webhooks"):
         tags.create_tag.return_value = tag_factory()
         api.tag_api.create_tag(
             context_factory(
diff --git a/server/szurubooru/tests/api/test_tag_deleting.py b/server/szurubooru/tests/api/test_tag_deleting.py
index b45ef556..59a19f8c 100644
--- a/server/szurubooru/tests/api/test_tag_deleting.py
+++ b/server/szurubooru/tests/api/test_tag_deleting.py
@@ -34,16 +34,17 @@ def test_deleting_used(
     post.tags.append(tag)
     db.session.add_all([tag, post])
     db.session.commit()
-    api.tag_api.delete_tag(
-        context_factory(
-            params={"version": 1},
-            user=user_factory(rank=model.User.RANK_REGULAR),
-        ),
-        {"tag_name": "tag"},
-    )
-    db.session.refresh(post)
-    assert db.session.query(model.Tag).count() == 0
-    assert post.tags == []
+    with patch("szurubooru.func.snapshots._post_to_webhooks"):
+        api.tag_api.delete_tag(
+            context_factory(
+                params={"version": 1},
+                user=user_factory(rank=model.User.RANK_REGULAR),
+            ),
+            {"tag_name": "tag"},
+        )
+        db.session.refresh(post)
+        assert db.session.query(model.Tag).count() == 0
+        assert post.tags == []
 
 
 def test_trying_to_delete_non_existing(user_factory, context_factory):
diff --git a/server/szurubooru/tests/func/test_net.py b/server/szurubooru/tests/func/test_net.py
index 58e16287..8539a343 100644
--- a/server/szurubooru/tests/func/test_net.py
+++ b/server/szurubooru/tests/func/test_net.py
@@ -1,3 +1,6 @@
+from datetime import datetime
+from unittest.mock import patch
+
 import pytest
 
 from szurubooru import errors
@@ -99,3 +102,45 @@ def test_video_download(url, expected_sha1):
 def test_failed_video_download(url):
     with pytest.raises(errors.ThirdPartyError):
         net.download(url, use_video_downloader=True)
+
+
+def test_no_webhooks(config_injector):
+    config_injector({"webhooks": []})
+    res = net.post_to_webhooks(None)
+    assert len(res) == 0
+
+
+@pytest.mark.parametrize(
+    "webhook,status_code",
+    [
+        ("https://postman-echo.com/post", 200),
+        ("http://localhost/", 400),
+        ("https://postman-echo.com/get", 400),
+    ],
+)
+def test_single_webhook(config_injector, webhook, status_code):
+    config_injector({"webhooks": [webhook]})
+    res = net.post_to_webhooks({"test_arg": "test_value"})
+    assert len(res) == 1
+    assert res[0] == status_code
+
+
+def test_multiple_webhooks(config_injector):
+    config_injector(
+        {
+            "webhooks": [
+                "https://postman-echo.com/post",
+                "https://postman-echo.com/post",
+            ]
+        }
+    )
+    res = net.post_to_webhooks({"test_arg": "test_value"})
+    assert len(res) == 2
+    assert res[0] == 200
+    assert res[1] == 200
+
+
+def test_malformed_webhooks(config_injector):
+    config_injector({"webhooks": ["malformed_url"]})
+    with pytest.raises(ValueError):
+        net.post_to_webhooks({"test_arg": "test_value"})
diff --git a/server/szurubooru/tests/func/test_snapshots.py b/server/szurubooru/tests/func/test_snapshots.py
index b4dda1cc..da935307 100644
--- a/server/szurubooru/tests/func/test_snapshots.py
+++ b/server/szurubooru/tests/func/test_snapshots.py
@@ -132,7 +132,9 @@ def test_create(tag_factory, user_factory):
     tag = tag_factory(names=["dummy"])
     db.session.add(tag)
     db.session.flush()
-    with patch("szurubooru.func.snapshots.get_tag_snapshot"):
+    with patch("szurubooru.func.snapshots.get_tag_snapshot"), patch(
+        "szurubooru.func.snapshots._post_to_webhooks"
+    ):
         snapshots.get_tag_snapshot.return_value = "mocked"
         snapshots.create(tag, user_factory())
     db.session.flush()
@@ -156,29 +158,30 @@ def test_modify_saves_non_empty_diffs(post_factory, user_factory):
     post.source = "new source"
     post.notes = [model.PostNote(polygon=[(0, 0), (0, 1), (1, 1)], text="new")]
     db.session.flush()
-    snapshots.modify(post, user)
-    db.session.flush()
-    results = db.session.query(model.Snapshot).all()
-    assert len(results) == 1
-    assert results[0].data == {
-        "type": "object change",
-        "value": {
-            "source": {
-                "type": "primitive change",
-                "old-value": None,
-                "new-value": "new source",
+    with patch("szurubooru.func.snapshots._post_to_webhooks"):
+        snapshots.modify(post, user)
+        db.session.flush()
+        results = db.session.query(model.Snapshot).all()
+        assert len(results) == 1
+        assert results[0].data == {
+            "type": "object change",
+            "value": {
+                "source": {
+                    "type": "primitive change",
+                    "old-value": None,
+                    "new-value": "new source",
+                },
+                "notes": {
+                    "type": "list change",
+                    "removed": [
+                        {"polygon": [[0, 0], [0, 1], [1, 1]], "text": "old"}
+                    ],
+                    "added": [
+                        {"polygon": [[0, 0], [0, 1], [1, 1]], "text": "new"}
+                    ],
+                },
             },
-            "notes": {
-                "type": "list change",
-                "removed": [
-                    {"polygon": [[0, 0], [0, 1], [1, 1]], "text": "old"}
-                ],
-                "added": [
-                    {"polygon": [[0, 0], [0, 1], [1, 1]], "text": "new"}
-                ],
-            },
-        },
-    }
+        }
 
 
 def test_modify_doesnt_save_empty_diffs(tag_factory, user_factory):
@@ -195,7 +198,9 @@ def test_delete(tag_factory, user_factory):
     tag = tag_factory(names=["dummy"])
     db.session.add(tag)
     db.session.flush()
-    with patch("szurubooru.func.snapshots.get_tag_snapshot"):
+    with patch("szurubooru.func.snapshots.get_tag_snapshot"), patch(
+        "szurubooru.func.snapshots._post_to_webhooks"
+    ):
         snapshots.get_tag_snapshot.return_value = "mocked"
         snapshots.delete(tag, user_factory())
     db.session.flush()
@@ -210,8 +215,9 @@ def test_merge(tag_factory, user_factory):
     target_tag = tag_factory(names=["target"])
     db.session.add_all([source_tag, target_tag])
     db.session.flush()
-    snapshots.merge(source_tag, target_tag, user_factory())
-    db.session.flush()
-    result = db.session.query(model.Snapshot).one()
-    assert result.operation == model.Snapshot.OPERATION_MERGED
-    assert result.data == ["tag", "target"]
+    with patch("szurubooru.func.snapshots._post_to_webhooks"):
+        snapshots.merge(source_tag, target_tag, user_factory())
+        db.session.flush()
+        result = db.session.query(model.Snapshot).one()
+        assert result.operation == model.Snapshot.OPERATION_MERGED
+        assert result.data == ["tag", "target"]