diff --git a/libs/gql-schema/organization-settings.ts b/libs/gql-schema/organization-settings.ts
index b3110fca4..326e4b2d4 100644
--- a/libs/gql-schema/organization-settings.ts
+++ b/libs/gql-schema/organization-settings.ts
@@ -13,6 +13,7 @@ export const schema = `
     showDoNotAssignMessage: Boolean
     doNotAssignMessage: String
     defaultAutosendingControlsMode: AutosendingControlsMode
+    maxSmsSegmentLength: Int
 
     # Superadmin
     startCampaignRequiresApproval: Boolean
@@ -28,6 +29,7 @@ export const schema = `
     confirmationClickForScriptLinks: Boolean!
     showDoNotAssignMessage: Boolean!
     doNotAssignMessage: String!
+    maxSmsSegmentLength: Int
 
     # Supervolunteer
     startCampaignRequiresApproval: Boolean
diff --git a/libs/spoke-codegen/src/graphql/general-settings.graphql b/libs/spoke-codegen/src/graphql/general-settings.graphql
index 96a20c03e..bd2cf064c 100644
--- a/libs/spoke-codegen/src/graphql/general-settings.graphql
+++ b/libs/spoke-codegen/src/graphql/general-settings.graphql
@@ -76,3 +76,26 @@ mutation UpdateAutosendingSettings(
     defaultAutosendingControlsMode
   }
 }
+
+query GetMessageSendingSettings($organizationId: String!) {
+  organization(id: $organizationId) {
+    id
+    settings {
+      id
+      maxSmsSegmentLength
+    }
+  }
+}
+
+mutation UpdateMessageSendingSettings(
+  $organizationId: String!
+  $maxSmsSegmentLength: Int
+) {
+  editOrganizationSettings(
+    id: $organizationId
+    input: { maxSmsSegmentLength: $maxSmsSegmentLength }
+  ) {
+    id
+    maxSmsSegmentLength
+  }
+}
diff --git a/libs/spoke-codegen/src/graphql/spoke-context.graphql b/libs/spoke-codegen/src/graphql/spoke-context.graphql
index 61f05a4a9..ccdc523c8 100644
--- a/libs/spoke-codegen/src/graphql/spoke-context.graphql
+++ b/libs/spoke-codegen/src/graphql/spoke-context.graphql
@@ -20,4 +20,5 @@ fragment OrganizationSettingsInfo on OrganizationSettings {
   scriptPreviewForSupervolunteers
   defaultCampaignBuilderMode
   defaultAutosendingControlsMode
+  maxSmsSegmentLength
 }
diff --git a/src/containers/Settings/components/General.jsx b/src/containers/Settings/components/General.jsx
index d6c6a93da..5f55b990b 100644
--- a/src/containers/Settings/components/General.jsx
+++ b/src/containers/Settings/components/General.jsx
@@ -25,6 +25,7 @@ import { loadData } from "../../hoc/with-operations";
 import AutosendingSettingsCard from "./AutosendingSettingsCard";
 import CampaignBuilderSettingsCard from "./CampaignBuilderSettingsCard";
 import EditName from "./EditName";
+import MessageSendingSettingsCard from "./MessageSendingSettingsCard";
 import RejectedTextersMessageCard from "./RejectedTextersMessageCard";
 import Review10DlcInfo from "./Review10DlcInfo";
 import ScriptPreviewSettingsCard from "./ScriptPreviewSettingsCard";
@@ -473,6 +474,11 @@ class Settings extends React.Component {
           style={{ marginBottom: 20 }}
         />
 
+        <MessageSendingSettingsCard
+          organizationId={organization.id}
+          style={{ marginBottom: 20 }}
+        />
+
         {window.ENABLE_TROLLBOT && (
           <Card className={css(styles.sectionCard)}>
             <GSForm
diff --git a/src/containers/Settings/components/MessageSendingSettingsCard.tsx b/src/containers/Settings/components/MessageSendingSettingsCard.tsx
new file mode 100644
index 000000000..982efba2d
--- /dev/null
+++ b/src/containers/Settings/components/MessageSendingSettingsCard.tsx
@@ -0,0 +1,117 @@
+import Card from "@material-ui/core/Card";
+import CardContent from "@material-ui/core/CardContent";
+import CardHeader from "@material-ui/core/CardHeader";
+import FormControlLabel from "@material-ui/core/FormControlLabel";
+import Switch from "@material-ui/core/Switch";
+import TextField from "@material-ui/core/TextField";
+import Alert from "@material-ui/lab/Alert";
+import {
+  useGetMessageSendingSettingsQuery,
+  useUpdateMessageSendingSettingsMutation
+} from "@spoke/spoke-codegen";
+import React from "react";
+
+export interface MessageSendingSettingsCardProps {
+  organizationId: string;
+  style?: React.CSSProperties;
+}
+
+// eslint-disable-next-line max-len
+export const MessageSendingSettingsCard: React.FC<MessageSendingSettingsCardProps> = (
+  props
+) => {
+  const { organizationId, style } = props;
+
+  const getSettingsState = useGetMessageSendingSettingsQuery({
+    variables: { organizationId }
+  });
+  const settings = getSettingsState?.data?.organization?.settings;
+
+  const [
+    setMaxSmsSegmentLength,
+    updateState
+  ] = useUpdateMessageSendingSettingsMutation();
+
+  const working = getSettingsState.loading || updateState.loading;
+  const errorMsg =
+    getSettingsState.error?.message ?? updateState.error?.message;
+
+  const maxSmsSegmentLength = settings?.maxSmsSegmentLength;
+  const showMaxSmsSegmentLength = maxSmsSegmentLength !== null;
+
+  const setNewMaxSmsSegmentLength = async (
+    newMax: number | null | undefined
+  ) => {
+    await setMaxSmsSegmentLength({
+      variables: {
+        organizationId,
+        maxSmsSegmentLength: newMax
+      }
+    });
+  };
+
+  // eslint-disable-next-line max-len
+  const handleChangeMaxSmsSegmentLength: React.ChangeEventHandler<HTMLInputElement> = async (
+    event
+  ) => {
+    if (working) return;
+    const newMax = event.target.valueAsNumber;
+    await setNewMaxSmsSegmentLength(newMax);
+  };
+
+  // eslint-disable-next-line max-len
+  const handleToggleMmsConversion: React.ChangeEventHandler<HTMLInputElement> = async (
+    event
+  ) => {
+    const { checked } = event.target;
+    const DEFAULT_MAX_SMS_SEGMENT_LENGTH = 3;
+    const newMax = checked ? DEFAULT_MAX_SMS_SEGMENT_LENGTH : null;
+    await setNewMaxSmsSegmentLength(newMax);
+  };
+
+  return (
+    <Card style={style}>
+      <CardHeader title="Message Sending Settings" disableTypography />
+      <CardContent>
+        {errorMsg && <Alert severity="error">Error: {errorMsg}</Alert>}
+        <p>
+          Turn on this feature to automatically convert long SMS messages to
+          MMS. If turned on, SMS messages <i>longer</i> than the length you set
+          will be converted. For example, if you set the max length to 3, a 4
+          segment SMS message will be converted to MMS.
+        </p>
+        <p style={{ marginBottom: 25 }}>
+          Messages longer than 3 segments are usually cheaper to send as MMS.
+          You may notice changes in deliverability when switching from SMS to
+          MMS messages.{" "}
+          <a
+            href="https://docs.spokerewired.com/article/86-include-an-image-in-a-message"
+            target="_blank"
+            rel="noopener noreferrer"
+          >
+            Learn more about sending MMS here
+          </a>
+        </p>
+        <FormControlLabel
+          label="Convert long SMS messages to MMS?"
+          control={
+            <Switch
+              checked={showMaxSmsSegmentLength}
+              onChange={handleToggleMmsConversion}
+            />
+          }
+        />
+        {showMaxSmsSegmentLength && (
+          <TextField
+            label="Max SMS Segment Length"
+            type="number"
+            value={settings?.maxSmsSegmentLength}
+            onChange={handleChangeMaxSmsSegmentLength}
+          />
+        )}
+      </CardContent>
+    </Card>
+  );
+};
+
+export default MessageSendingSettingsCard;
diff --git a/src/schema.graphql b/src/schema.graphql
index ea14a2ca9..a11696ae1 100644
--- a/src/schema.graphql
+++ b/src/schema.graphql
@@ -482,6 +482,7 @@ input OrganizationSettingsInput {
   showDoNotAssignMessage: Boolean
   doNotAssignMessage: String
   defaultAutosendingControlsMode: AutosendingControlsMode
+  maxSmsSegmentLength: Int
 
   # Superadmin
   startCampaignRequiresApproval: Boolean
@@ -497,6 +498,7 @@ type OrganizationSettings {
   confirmationClickForScriptLinks: Boolean!
   showDoNotAssignMessage: Boolean!
   doNotAssignMessage: String!
+  maxSmsSegmentLength: Int
 
   # Supervolunteer
   startCampaignRequiresApproval: Boolean
diff --git a/src/server/api/lib/assemble-numbers.ts b/src/server/api/lib/assemble-numbers.ts
index 40b00e8ed..a6aa9bd9d 100644
--- a/src/server/api/lib/assemble-numbers.ts
+++ b/src/server/api/lib/assemble-numbers.ts
@@ -1,5 +1,6 @@
 import type { Knex } from "knex";
 import type { PoolClient } from "pg";
+import { getSpokeCharCount } from "src/lib/charset-utils";
 
 import { config } from "../../../config";
 import { getFormattedPhoneNumber } from "../../../lib/phone-format";
@@ -177,8 +178,24 @@ export const sendMessage = async (
     .reader("campaign_contact")
     .where({ id: campaignContactId })
     .first("zip");
+
+  const { maxSmsSegmentLength } = await r
+    .reader("organization")
+    .where({ id: organizationId })
+    .first("features")
+    .then(({ features }: { features: string }) => JSON.parse(features))
+    .catch(() => ({}));
+
   const { body, mediaUrl } = messageComponents(messageText);
-  const mediaUrls = mediaUrl ? [mediaUrl] : undefined;
+  const { msgCount } = getSpokeCharCount(messageText);
+
+  const mediaUrls = mediaUrl
+    ? [mediaUrl]
+    : // format for switchboard to send empty MMS
+    maxSmsSegmentLength && msgCount > maxSmsSegmentLength
+    ? []
+    : undefined;
+
   const messageInput: NumbersOutboundMessagePayload = {
     profileId,
     to,
@@ -188,6 +205,8 @@ export const sendMessage = async (
     contactZipCode: contactZipCode === "" ? null : contactZipCode
   };
 
+  console.log(messageInput);
+
   try {
     const result = await numbers.sms.sendMessage(messageInput);
     const { data, errors } = result;
diff --git a/src/server/api/organization-settings.ts b/src/server/api/organization-settings.ts
index 5f0f21205..7245703ad 100644
--- a/src/server/api/organization-settings.ts
+++ b/src/server/api/organization-settings.ts
@@ -28,6 +28,7 @@ interface IOrganizationSettings {
   doNotAssignMessage: string;
   defaultCampaignBuilderMode: CampaignBuilderMode;
   defaultAutosendingControlsMode: AutosendingControlsMode;
+  maxSmsSegmentLength: number | null;
 }
 
 const SETTINGS_PERMISSIONS: {
@@ -45,7 +46,8 @@ const SETTINGS_PERMISSIONS: {
   defaultAutosendingControlsMode: UserRoleType.ADMIN,
   defaulTexterApprovalStatus: UserRoleType.OWNER,
   numbersApiKey: UserRoleType.OWNER,
-  trollbotWebhookUrl: UserRoleType.OWNER
+  trollbotWebhookUrl: UserRoleType.OWNER,
+  maxSmsSegmentLength: UserRoleType.TEXTER
 };
 
 const SETTINGS_WRITE_PERMISSIONS: {
@@ -63,7 +65,8 @@ const SETTINGS_WRITE_PERMISSIONS: {
   showDoNotAssignMessage: UserRoleType.OWNER,
   doNotAssignMessage: UserRoleType.OWNER,
   defaultAutosendingControlsMode: UserRoleType.OWNER,
-  startCampaignRequiresApproval: UserRoleType.SUPERADMIN
+  startCampaignRequiresApproval: UserRoleType.SUPERADMIN,
+  maxSmsSegmentLength: UserRoleType.OWNER
 };
 
 const SETTINGS_NAMES: Partial<
@@ -86,7 +89,8 @@ const SETTINGS_DEFAULTS: IOrganizationSettings = {
   doNotAssignMessage:
     "Your ability to request texts has been put on hold. Please a contact a text team leader for more information.",
   defaultCampaignBuilderMode: CampaignBuilderMode.Advanced,
-  defaultAutosendingControlsMode: AutosendingControlsMode.Detailed
+  defaultAutosendingControlsMode: AutosendingControlsMode.Detailed,
+  maxSmsSegmentLength: 3
 };
 
 const SETTINGS_TRANSFORMERS: Partial<
@@ -133,13 +137,17 @@ export const getOrgFeature = <T extends keyof IOrganizationSettings>(
   const finalName = SETTINGS_NAMES[featureName] ?? featureName;
   try {
     const features = JSON.parse(rawFeatures);
-    const value = features[finalName] ?? defaultValue ?? null;
+
+    const foundValue = features[finalName];
+    const returnValue =
+      foundValue === undefined ? defaultValue ?? null : foundValue;
+
     const transformer = SETTINGS_TRANSFORMERS[featureName];
-    if (transformer && value) {
-      const result = transformer(value);
+    if (transformer && returnValue) {
+      const result = transformer(returnValue);
       return result as IOrganizationSettings[T];
     }
-    return value;
+    return returnValue;
   } catch (_err) {
     return SETTINGS_DEFAULTS[featureName] ?? null;
   }
@@ -183,7 +191,8 @@ export const resolvers = {
       "defaultCampaignBuilderMode",
       "showDoNotAssignMessage",
       "doNotAssignMessage",
-      "defaultAutosendingControlsMode"
+      "defaultAutosendingControlsMode",
+      "maxSmsSegmentLength"
     ])
   }
 };
diff --git a/src/server/organization-settings.spec.ts b/src/server/organization-settings.spec.ts
index ae9337ccc..73400714b 100644
--- a/src/server/organization-settings.spec.ts
+++ b/src/server/organization-settings.spec.ts
@@ -37,7 +37,8 @@ describe("get organization settings", () => {
     defaultAutosendingControlsMode: AutosendingControlsMode.Basic,
     defaulTexterApprovalStatus: RequestAutoApproveType.APPROVAL_REQUIRED,
     numbersApiKey: "SomethingSecret",
-    trollbotWebhookUrl: "https://rewired.coop/trolls"
+    trollbotWebhookUrl: "https://rewired.coop/trolls",
+    maxSmsSegmentLength: 3
   };
 
   const makeSettingsRequest = async (
@@ -68,6 +69,7 @@ describe("get organization settings", () => {
                 defaulTexterApprovalStatus
                 numbersApiKey
                 trollbotWebhookUrl
+                maxSmsSegmentLength
               }
             }
           }
@@ -135,6 +137,7 @@ describe("get organization settings", () => {
     );
     expect(settings.numbersApiKey).not.toBeNull();
     expect(settings.trollbotWebhookUrl).toEqual(features.trollbotWebhookUrl);
+    expect(settings.maxSmsSegmentLength).toEqual(features.maxSmsSegmentLength);
   });
 
   it("returns the correct role required", () => {