diff --git a/packages/api/handlers/update-guild.ts b/packages/api/handlers/update-guild.ts
index 0c37729..c4985b8 100644
--- a/packages/api/handlers/update-guild.ts
+++ b/packages/api/handlers/update-guild.ts
@@ -1,8 +1,20 @@
-import { GuildDataUpdate, SessionData, UserGuildPermissions } from '@roleypoly/types';
+import { sendAuditLog, validateAuditLogWebhook } from '@roleypoly/api/utils/audit-log';
+import {
+  GuildDataUpdate,
+  SessionData,
+  UserGuildPermissions,
+  WebhookValidationStatus,
+} from '@roleypoly/types';
 import { withSession } from '../utils/api-tools';
 import { getGuildData } from '../utils/guild';
 import { GuildData } from '../utils/kv';
-import { lowPermissions, missingParameters, notFound, ok } from '../utils/responses';
+import {
+  invalid,
+  lowPermissions,
+  missingParameters,
+  notFound,
+  ok,
+} from '../utils/responses';
 
 export const UpdateGuild = withSession(
   (session: SessionData) =>
@@ -27,13 +39,42 @@ export const UpdateGuild = withSession(
         return lowPermissions();
       }
 
+      const oldGuildData = await getGuildData(guildID);
       const newGuildData = {
-        ...(await getGuildData(guildID)),
+        ...oldGuildData,
         ...guildUpdate,
       };
 
+      if (oldGuildData.auditLogWebhook !== newGuildData.auditLogWebhook) {
+        try {
+          const validationStatus = await validateAuditLogWebhook(
+            guild,
+            newGuildData.auditLogWebhook
+          );
+
+          if (validationStatus !== WebhookValidationStatus.Ok) {
+            if (validationStatus === WebhookValidationStatus.NoneSet) {
+              newGuildData.auditLogWebhook = null;
+            } else {
+              return invalid({
+                what: 'webhookValidationStatus',
+                webhookValidationStatus: validationStatus,
+              });
+            }
+          }
+        } catch (e) {
+          invalid();
+        }
+      }
+
       await GuildData.put(guildID, newGuildData);
 
+      try {
+        await sendAuditLog(oldGuildData, guildUpdate, session.user);
+      } catch (e) {
+        // Catching errors here because this isn't a critical task, and could simply fail due to operator error.
+      }
+
       return ok();
     }
 );
diff --git a/packages/api/package.json b/packages/api/package.json
index 5ff6f12..b5d0aee 100644
--- a/packages/api/package.json
+++ b/packages/api/package.json
@@ -11,6 +11,8 @@
     "@roleypoly/misc-utils": "*",
     "@roleypoly/types": "*",
     "@roleypoly/worker-emulator": "*",
+    "@types/deep-equal": "^1.0.1",
+    "deep-equal": "^2.0.5",
     "ksuid": "^2.0.0",
     "lodash": "^4.17.21",
     "ts-loader": "^8.3.0"
diff --git a/packages/api/utils/audit-log.ts b/packages/api/utils/audit-log.ts
new file mode 100644
index 0000000..e7c175f
--- /dev/null
+++ b/packages/api/utils/audit-log.ts
@@ -0,0 +1,226 @@
+import { userAgent } from '@roleypoly/api/utils/api-tools';
+import { uiPublicURI } from '@roleypoly/api/utils/config';
+import {
+  Category,
+  DiscordUser,
+  GuildData,
+  GuildDataUpdate,
+  GuildSlug,
+  WebhookValidationStatus,
+} from '@roleypoly/types';
+import deepEqual from 'deep-equal';
+import { sortBy, uniq } from 'lodash';
+
+type WebhookEmbed = {
+  fields: {
+    name: string;
+    value: string;
+    inline: boolean;
+  }[];
+  timestamp: string;
+  title: string;
+  color: number;
+  author?: {
+    name: string;
+    icon_url: string;
+  };
+};
+
+type WebhookPayload = {
+  username: string;
+  avatar_url: string;
+  embeds: WebhookEmbed[];
+  provider: {
+    name: string;
+    url: string;
+  };
+};
+
+type ChangeHandler = (
+  oldValue: GuildDataUpdate[keyof GuildDataUpdate],
+  newValue: GuildData[keyof GuildDataUpdate]
+) => WebhookEmbed[];
+
+const changeHandlers: Record<keyof GuildDataUpdate, ChangeHandler> = {
+  message: (oldValue, newValue) => [
+    {
+      timestamp: new Date().toISOString(),
+      color: 0x453e3d,
+      fields: [
+        {
+          name: 'Old Message',
+          value: oldValue as string,
+          inline: false,
+        },
+        {
+          name: 'New Message',
+          value: newValue as string,
+          inline: false,
+        },
+      ],
+      title: `Server message was updated...`,
+    },
+  ],
+  auditLogWebhook: (oldValue, newValue) => [
+    {
+      timestamp: new Date().toISOString(),
+      color: 0x5d5352,
+      fields: [
+        {
+          name: 'Old Webhook ID',
+          value: !oldValue ? '*unset*' : (oldValue as string).split('/')[5],
+          inline: false,
+        },
+        {
+          name: 'New Webhook ID',
+          value: !newValue ? '*unset*' : (newValue as string).split('/')[5],
+          inline: false,
+        },
+      ],
+      title: `Audit Log webhook URL was changed...`,
+    },
+  ],
+  categories: (oldValue, newValue) => [
+    {
+      timestamp: new Date().toISOString(),
+      color: 0xab9b9a,
+      fields: [
+        {
+          name: 'Changed Categories',
+          value: getChangedCategories(
+            oldValue as Category[],
+            newValue as Category[]
+          ).join('\n'),
+          inline: false,
+        },
+      ],
+      title: `Categories were changed...`,
+    },
+  ],
+};
+
+export const sendAuditLog = async (
+  guild: GuildData,
+  guildUpdate: GuildDataUpdate,
+  user: DiscordUser
+) => {
+  const auditLogWebhooks = uniq([
+    guild.auditLogWebhook || '',
+    guildUpdate.auditLogWebhook || '',
+  ]).filter((webhook) => webhook !== '');
+
+  if (auditLogWebhooks.length === 0) {
+    return;
+  }
+
+  const keys = Object.keys(guildUpdate) as (keyof GuildDataUpdate)[];
+  const webhookPayload: WebhookPayload = {
+    username: 'Roleypoly (Audit Log)',
+    avatar_url: `https://next.roleypoly.com/logo192.png`, //TODO: change to roleypoly.com when swapped.
+    embeds: [
+      {
+        fields: [],
+        timestamp: new Date().toISOString(),
+        title: `${user.username}#${user.discriminator} has edited Roleypoly settings`,
+        color: 0x332d2d,
+        author: {
+          name: user.username,
+          icon_url: `https://cdn.discordapp.com/avatars/${user.id}/${user.avatar}.png`,
+        },
+      },
+    ],
+    provider: {
+      name: 'Roleypoly',
+      url: uiPublicURI,
+    },
+  };
+
+  for (let key of keys) {
+    if (deepEqual(guildUpdate[key], guild[key])) {
+      continue;
+    }
+
+    const handler = changeHandlers[key];
+    if (!handler) {
+      continue;
+    }
+
+    const changeFields = handler(guild[key], guildUpdate[key]);
+    webhookPayload.embeds.push(...changeFields);
+  }
+
+  if (webhookPayload.embeds.length === 1) {
+    // No changes, don't bother sending
+    return;
+  }
+
+  // Colors are in order already, so use them to order the embeds.
+  webhookPayload.embeds = sortBy(webhookPayload.embeds, 'color');
+
+  const doWebhook = (webhook: string) =>
+    fetch(webhook, {
+      method: 'POST',
+      body: JSON.stringify(webhookPayload),
+      headers: {
+        'content-type': 'application/json',
+        'user-agent': userAgent,
+      },
+    });
+
+  await Promise.all(auditLogWebhooks.map((webhook) => doWebhook(webhook)));
+};
+
+export const validateAuditLogWebhook = async (
+  guild: GuildSlug,
+  webhook: string | null
+): Promise<WebhookValidationStatus> => {
+  if (!webhook) {
+    return WebhookValidationStatus.NoneSet;
+  }
+
+  const url = new URL(webhook);
+
+  if (
+    url.hostname !== 'discord.com' ||
+    url.protocol !== 'https:' ||
+    url.pathname.startsWith('api/webhooks/')
+  ) {
+    return WebhookValidationStatus.NotDiscordURL;
+  }
+
+  const response = await fetch(webhook, { method: 'GET' });
+  if (response.status !== 200) {
+    return WebhookValidationStatus.DoesNotExist;
+  }
+
+  const webhookData = await response.json();
+
+  if (webhookData.guild_id !== guild.id) {
+    return WebhookValidationStatus.NotSameGuild;
+  }
+
+  return WebhookValidationStatus.Ok;
+};
+
+const getChangedCategories = (oldCategories: Category[], newCategories: Category[]) => {
+  const addedCategories = newCategories.filter(
+    (c) => !oldCategories.find((o) => o.id === c.id)
+  );
+  const removedCategories = oldCategories.filter(
+    (c) => !newCategories.find((o) => o.id === c.id)
+  );
+  const changedCategories = newCategories.filter(
+    (c) =>
+      oldCategories.find((o) => o.id === c.id) &&
+      !deepEqual(
+        oldCategories.find((o) => o.id === c.id),
+        newCategories.find((o) => o.id === c.id)
+      )
+  );
+
+  return [
+    ...addedCategories.map((c) => `➕ **Added** ${c.name}`),
+    ...removedCategories.map((c) => `➖ **Removed** ${c.name}`),
+    ...changedCategories.map((c) => `🔧 **Changed** ${c.name}`),
+  ];
+};
diff --git a/packages/api/utils/guild.ts b/packages/api/utils/guild.ts
index de92f4b..0f37438 100644
--- a/packages/api/utils/guild.ts
+++ b/packages/api/utils/guild.ts
@@ -128,17 +128,22 @@ export const updateGuildMemberRoles = async (
 
 export const getGuildData = async (id: string): Promise<GuildDataT> => {
   const guildData = await GuildData.get<GuildDataT>(id);
+  const empty = {
+    id,
+    message: '',
+    categories: [],
+    features: Features.None,
+    auditLogWebhook: null,
+  };
 
   if (!guildData) {
-    return {
-      id,
-      message: '',
-      categories: [],
-      features: Features.None,
-    };
+    return empty;
   }
 
-  return guildData;
+  return {
+    ...empty,
+    ...guildData,
+  };
 };
 
 const calculateRoleSafety = (role: Role | APIRole, highestBotRolePosition: number) => {
diff --git a/packages/api/utils/responses.ts b/packages/api/utils/responses.ts
index 7b8936b..7838d6d 100644
--- a/packages/api/utils/responses.ts
+++ b/packages/api/utils/responses.ts
@@ -14,3 +14,6 @@ export const conflict = () => respond({ error: 'conflict' }, { status: 409 });
 
 export const rateLimited = () =>
   respond({ error: 'rate limit hit, enhance your calm' }, { status: 419 });
+
+export const invalid = (obj: any = {}) =>
+  respond({ err: 'client sent something invalid', data: obj }, { status: 400 });
diff --git a/packages/design-system/atoms/space/Space.stories.tsx b/packages/design-system/atoms/space/Space.stories.tsx
index ac0e768..d21882e 100644
--- a/packages/design-system/atoms/space/Space.stories.tsx
+++ b/packages/design-system/atoms/space/Space.stories.tsx
@@ -1,14 +1,22 @@
 import * as React from 'react';
-import { Space as SpaceComponent } from './Space';
+import { LinedSpace, Space } from './Space';
 
 export default {
-  title: 'Atoms',
+  title: 'Atoms/Space',
 };
 
-export const Space = () => (
+export const space = () => (
   <>
     hello world
-    <SpaceComponent />
+    <Space />
+    but im over here
+  </>
+);
+
+export const linedSpace = () => (
+  <>
+    hello world
+    <LinedSpace />
     but im over here
   </>
 );
diff --git a/packages/design-system/atoms/space/Space.tsx b/packages/design-system/atoms/space/Space.tsx
index 84b8d7e..15c27a6 100644
--- a/packages/design-system/atoms/space/Space.tsx
+++ b/packages/design-system/atoms/space/Space.tsx
@@ -1,5 +1,17 @@
-import styled from 'styled-components';
+import { palette } from '@roleypoly/design-system/atoms/colors';
+import styled, { css } from 'styled-components';
 
 export const Space = styled.div`
   height: 15px;
 `;
+
+export const LinedSpace = styled.div<{ width?: number }>`
+  height: 7.5px;
+  margin-top: 7.5px;
+  border-top: 1px solid ${palette.taupe300};
+  ${(props) =>
+    props.width &&
+    css`
+      width: ${props.width}px;
+    `}
+`;
diff --git a/packages/design-system/molecules/server-utilities/ServerUtilities.tsx b/packages/design-system/molecules/server-utilities/ServerUtilities.tsx
new file mode 100644
index 0000000..ed9a385
--- /dev/null
+++ b/packages/design-system/molecules/server-utilities/ServerUtilities.tsx
@@ -0,0 +1,72 @@
+import { palette } from '@roleypoly/design-system/atoms/colors';
+import { FaderOpacity } from '@roleypoly/design-system/atoms/fader';
+import { TextInput } from '@roleypoly/design-system/atoms/text-input';
+import { AmbientLarge, Text } from '@roleypoly/design-system/atoms/typography';
+import { MessageBox } from '@roleypoly/design-system/organisms/role-picker/RolePicker.styled';
+import { GuildData, WebhookValidationStatus } from '@roleypoly/types';
+import { GoAlert, GoInfo } from 'react-icons/go';
+import ReactTooltip from 'react-tooltip';
+import styled from 'styled-components';
+
+type Props = {
+  onChange: (guildData: GuildData) => void;
+  guildData: GuildData;
+  validationStatus: WebhookValidationStatus | null;
+};
+
+export const ServerUtilities = (props: Props) => {
+  return (
+    <MessageBox>
+      <Text>
+        (optional) Webhook URL for Audit Logging{' '}
+        <GoInfo
+          data-for="server-utilities"
+          data-tip="Reports changes made in the editor to a Webhook integration within your Discord server."
+        />
+      </Text>
+      <TextInput
+        placeholder="https://discord.com/api/webhooks/000000000000000000/..."
+        value={props.guildData.auditLogWebhook || ''}
+        onChange={(event) =>
+          props.onChange({ ...props.guildData, auditLogWebhook: event.target.value })
+        }
+      />
+      <FaderOpacity isVisible={props.validationStatus !== WebhookValidationStatus.Ok}>
+        <ValidationStatus validationStatus={props.validationStatus} />
+      </FaderOpacity>
+      <ReactTooltip id="server-utilities" />
+    </MessageBox>
+  );
+};
+
+const ValidationStatus = (props: Pick<Props, 'validationStatus'>) => {
+  switch (props.validationStatus) {
+    case WebhookValidationStatus.NotDiscordURL:
+      return (
+        <AmbientLarge>
+          <Alert /> URL must be to a Discord webhook, starting with
+          "https://discord.com/api/webhooks/".
+        </AmbientLarge>
+      );
+    case WebhookValidationStatus.NotSameGuild:
+      return (
+        <AmbientLarge>
+          <Alert /> Webhook must be in the same guild you are currently editing.
+        </AmbientLarge>
+      );
+    case WebhookValidationStatus.DoesNotExist:
+      return (
+        <AmbientLarge>
+          <Alert /> This webhook doesn't exist.
+        </AmbientLarge>
+      );
+    default:
+      return <AmbientLarge>&nbsp;</AmbientLarge>;
+  }
+};
+
+const Alert = styled(GoAlert)`
+  color: ${palette.red400};
+  position: relative;
+  top: 2px;
+`;
diff --git a/packages/design-system/organisms/editor-shell/EditorShell.tsx b/packages/design-system/organisms/editor-shell/EditorShell.tsx
index 48433b0..0258b00 100644
--- a/packages/design-system/organisms/editor-shell/EditorShell.tsx
+++ b/packages/design-system/organisms/editor-shell/EditorShell.tsx
@@ -1,10 +1,16 @@
-import { Space } from '@roleypoly/design-system/atoms/space';
+import { LinedSpace, Space } from '@roleypoly/design-system/atoms/space';
 import { EditableServerMessage } from '@roleypoly/design-system/molecules/editable-server-message';
 import { ServerMasthead } from '@roleypoly/design-system/molecules/server-masthead';
+import { ServerUtilities } from '@roleypoly/design-system/molecules/server-utilities/ServerUtilities';
 import { SecondaryEditing } from '@roleypoly/design-system/organisms/masthead';
 import { Container } from '@roleypoly/design-system/organisms/role-picker/RolePicker.styled';
 import { ServerCategoryEditor } from '@roleypoly/design-system/organisms/server-category-editor';
-import { Category, PresentableGuild } from '@roleypoly/types';
+import {
+  Category,
+  GuildData,
+  PresentableGuild,
+  WebhookValidationStatus,
+} from '@roleypoly/types';
 import deepEqual from 'deep-equal';
 import React from 'react';
 
@@ -13,17 +19,26 @@ export type EditorShellProps = {
   onGuildChange?: (guild: PresentableGuild) => void;
   onCategoryChange?: (category: Category) => void;
   onMessageChange?: (message: PresentableGuild['data']['message']) => void;
+  errors: {
+    webhookValidation: WebhookValidationStatus;
+  };
 };
 
 export const EditorShell = (props: EditorShellProps) => {
   const [guild, setGuild] = React.useState<PresentableGuild>(props.guild);
+  const [errors, setErrors] = React.useState<EditorShellProps['errors']>(props.errors);
 
   React.useEffect(() => {
     setGuild(props.guild);
   }, [props.guild]);
 
+  React.useEffect(() => {
+    setErrors(props.errors);
+  }, [props.errors]);
+
   const reset = () => {
     setGuild(props.guild);
+    setErrors({ webhookValidation: WebhookValidationStatus.Ok });
   };
 
   const replaceCategories = (categories: Category[]) => {
@@ -38,6 +53,12 @@ export const EditorShell = (props: EditorShellProps) => {
     });
   };
 
+  const updateGuildData = (data: PresentableGuild['data']) => {
+    setGuild((currentGuild) => {
+      return { ...currentGuild, data };
+    });
+  };
+
   const doSubmit = () => {
     props.onGuildChange?.(guild);
   };
@@ -65,7 +86,48 @@ export const EditorShell = (props: EditorShellProps) => {
         />
         <Space />
         <ServerCategoryEditor guild={guild} onChange={replaceCategories} />
+        <LinedSpace />
+        <ServerUtilities
+          guildData={guild.data}
+          onChange={updateGuildData}
+          validationStatus={validateWebhook(
+            guild.data.auditLogWebhook,
+            errors.webhookValidation
+          )}
+        />
       </Container>
     </>
   );
 };
+
+const validateWebhook = (
+  webhook: GuildData['auditLogWebhook'],
+  validationStatus: WebhookValidationStatus
+) => {
+  if (!webhook) {
+    return WebhookValidationStatus.NoneSet;
+  }
+
+  try {
+    const url = new URL(webhook);
+
+    if (
+      url.hostname !== 'discord.com' ||
+      url.protocol !== 'https:' ||
+      url.pathname.startsWith('api/webhooks/')
+    ) {
+      return WebhookValidationStatus.NotDiscordURL;
+    }
+  } catch (e) {
+    return WebhookValidationStatus.Ok;
+  }
+
+  if (
+    validationStatus !== WebhookValidationStatus.Ok &&
+    validationStatus !== WebhookValidationStatus.NoneSet
+  ) {
+    return validationStatus;
+  }
+
+  return WebhookValidationStatus.Ok;
+};
diff --git a/packages/design-system/templates/editor/Editor.stories.tsx b/packages/design-system/templates/editor/Editor.stories.tsx
index 0cd8c67..1f97291 100644
--- a/packages/design-system/templates/editor/Editor.stories.tsx
+++ b/packages/design-system/templates/editor/Editor.stories.tsx
@@ -14,6 +14,7 @@ export default {
     ),
   ],
   args: {
+    errors: { validationStatus: 0 },
     guilds: mastheadSlugs,
     user: user,
     guild: guildEnum.guilds[0],
diff --git a/packages/design-system/templates/editor/Editor.tsx b/packages/design-system/templates/editor/Editor.tsx
index 6e6169c..36d76d3 100644
--- a/packages/design-system/templates/editor/Editor.tsx
+++ b/packages/design-system/templates/editor/Editor.tsx
@@ -11,7 +11,9 @@ export const EditorTemplate = (
     props;
   return (
     <AppShell {...appShellProps} activeGuildId={guild.id} small double>
-      <EditorShell guild={guild} onGuildChange={onGuildChange} />
+      <EditorShell guild={guild} onGuildChange={onGuildChange} errors={props.errors} />
     </AppShell>
   );
 };
+
+export type EditorErrors = EditorShellProps['errors'];
diff --git a/packages/types/Guild.ts b/packages/types/Guild.ts
index 9561be7..0c7f6af 100644
--- a/packages/types/Guild.ts
+++ b/packages/types/Guild.ts
@@ -20,6 +20,7 @@ export type GuildData = {
   message: string;
   categories: Category[];
   features: Features;
+  auditLogWebhook: string | null;
 };
 
 export type GuildDataUpdate = Omit<Omit<GuildData, 'features'>, 'id'>;
@@ -48,3 +49,11 @@ export type GuildSlug = {
   icon: string;
   permissionLevel: UserGuildPermissions;
 };
+
+export enum WebhookValidationStatus {
+  Ok,
+  NoneSet,
+  DoesNotExist,
+  NotSameGuild,
+  NotDiscordURL,
+}
diff --git a/packages/web/src/pages/editor.tsx b/packages/web/src/pages/editor.tsx
index 63455d7..c123568 100644
--- a/packages/web/src/pages/editor.tsx
+++ b/packages/web/src/pages/editor.tsx
@@ -1,10 +1,11 @@
 import { navigate, Redirect } from '@reach/router';
-import { EditorTemplate } from '@roleypoly/design-system/templates/editor';
+import { EditorErrors, EditorTemplate } from '@roleypoly/design-system/templates/editor';
 import { GenericLoadingTemplate } from '@roleypoly/design-system/templates/generic-loading';
 import {
   GuildDataUpdate,
   PresentableGuild,
   UserGuildPermissions,
+  WebhookValidationStatus,
 } from '@roleypoly/types';
 import * as React from 'react';
 import { useAppShellProps } from '../contexts/app-shell/AppShellContext';
@@ -25,6 +26,9 @@ const Editor = (props: EditorProps) => {
 
   const [guild, setGuild] = React.useState<PresentableGuild | null | false>(null);
   const [pending, setPending] = React.useState(false);
+  const [errors, setErrors] = React.useState<EditorErrors>({
+    webhookValidation: WebhookValidationStatus.Ok,
+  });
 
   React.useEffect(() => {
     const shouldPullUncached = (): boolean => {
@@ -87,6 +91,7 @@ const Editor = (props: EditorProps) => {
     const updatePayload: GuildDataUpdate = {
       message: guild.data.message,
       categories: guild.data.categories,
+      auditLogWebhook: guild.data.auditLogWebhook,
     };
 
     const response = await authedFetch(`/update-guild/${serverID}`, {
@@ -96,16 +101,31 @@ const Editor = (props: EditorProps) => {
 
     if (response.status === 200) {
       setGuild(guild);
-      setPending(false);
+      navigate(`/s/${props.serverID}`);
     }
 
-    navigate(`/s/${props.serverID}`);
+    if (response.status === 400) {
+      const error = await response.json();
+      if (error.data.what === 'webhookValidationStatus') {
+        setErrors((errors) => ({
+          ...errors,
+          webhookValidation: error.data.webhookValidationStatus,
+        }));
+      }
+    }
+
+    setPending(false);
   };
 
   return (
     <>
       <Title title={`Editing ${guild.guild.name} - Roleypoly`} />
-      <EditorTemplate {...appShellProps} guild={guild} onGuildChange={onGuildChange} />
+      <EditorTemplate
+        {...appShellProps}
+        guild={guild}
+        onGuildChange={onGuildChange}
+        errors={errors}
+      />
     </>
   );
 };