diff --git a/changes/issue-18848-include-all-exclude-any-custom-profile b/changes/issue-18848-include-all-exclude-any-custom-profile
new file mode 100644
index 0000000000..ef065303f3
--- /dev/null
+++ b/changes/issue-18848-include-all-exclude-any-custom-profile
@@ -0,0 +1,2 @@
+- add UI for uploading custom profiles with a target of hosts that include all/exclude
+  any selected labels
diff --git a/frontend/interfaces/config.ts b/frontend/interfaces/config.ts
index ebb286630c..21ac95dbcd 100644
--- a/frontend/interfaces/config.ts
+++ b/frontend/interfaces/config.ts
@@ -29,6 +29,12 @@ export interface IMacOsMigrationSettings {
   webhook_url: string;
 }
 
+interface ICustomSetting {
+  path: string;
+  labels_include_all?: string[];
+  labels_exclude_any?: string[];
+}
+
 export interface IMdmConfig {
   enable_disk_encryption: boolean;
   enabled_and_configured: boolean;
@@ -42,7 +48,7 @@ export interface IMdmConfig {
     deadline: string | null;
   };
   macos_settings: {
-    custom_settings: null;
+    custom_settings: null | ICustomSetting[];
     enable_disk_encryption: boolean;
   };
   macos_setup: {
diff --git a/frontend/interfaces/dropdownOption.ts b/frontend/interfaces/dropdownOption.ts
index a8895d48b9..67b1bacd4d 100644
--- a/frontend/interfaces/dropdownOption.ts
+++ b/frontend/interfaces/dropdownOption.ts
@@ -1,3 +1,4 @@
+import { ReactNode } from "react";
 import PropTypes from "prop-types";
 
 export default PropTypes.shape({
@@ -10,6 +11,7 @@ export interface IDropdownOption {
   disabled?: boolean;
   label: string | JSX.Element;
   value: string | number;
+  helpText?: ReactNode;
   premiumOnly?: boolean;
   tooltipContent?: string | JSX.Element;
 }
diff --git a/frontend/interfaces/mdm.ts b/frontend/interfaces/mdm.ts
index 4b3a8791e6..a911f0c9e7 100644
--- a/frontend/interfaces/mdm.ts
+++ b/frontend/interfaces/mdm.ts
@@ -71,7 +71,8 @@ export type ProfilePlatform = "darwin" | "windows";
 
 export interface IProfileLabel {
   name: string;
-  broken: boolean;
+  id?: number; // id is only present when the label is not broken
+  broken?: boolean;
 }
 
 export interface IMdmProfile {
@@ -83,7 +84,8 @@ export interface IMdmProfile {
   created_at: string;
   updated_at: string;
   checksum: string | null; // null for windows profiles
-  labels?: IProfileLabel[];
+  labels_include_all?: IProfileLabel[];
+  labels_exclude_any?: IProfileLabel[];
 }
 
 export type MdmProfileStatus = "verified" | "verifying" | "pending" | "failed";
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/CustomSettings.tsx b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/CustomSettings.tsx
index 8298a10647..89887e9b83 100644
--- a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/CustomSettings.tsx
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/CustomSettings.tsx
@@ -20,7 +20,7 @@ import Pagination from "pages/ManageControlsPage/components/Pagination";
 import UploadList from "../../../components/UploadList";
 
 import AddProfileCard from "./components/ProfileUploader/components/AddProfileCard";
-import AddProfileModal from "./components/ProfileUploader/components/AddProfileModal";
+import AddProfileModal from "./components/ProfileUploader/components/AddProfileModal/AddProfileModal";
 import DeleteProfileModal from "./components/DeleteProfileModal/DeleteProfileModal";
 import ProfileLabelsModal from "./components/ProfileLabelsModal/ProfileLabelsModal";
 import ProfileListItem from "./components/ProfileListItem";
@@ -101,7 +101,7 @@ const CustomSettings = ({
       onMutation();
       renderFlash("success", "Successfully deleted!");
     } catch (e) {
-      renderFlash("error", "Couldn’t delete. Please try again.");
+      renderFlash("error", "Couldn't delete. Please try again.");
     } finally {
       selectedProfile.current = null;
       setShowDeleteProfileModal(false);
@@ -169,6 +169,10 @@ const CustomSettings = ({
     );
   };
 
+  const hasLabels =
+    !!profileLabelsModalData?.labels_include_all?.length ||
+    !!profileLabelsModalData?.labels_exclude_any?.length;
+
   return (
     <div className={baseClass}>
       <SectionHeader title="Custom settings" />
@@ -189,7 +193,6 @@ const CustomSettings = ({
       )}
       {showAddProfileModal && (
         <AddProfileModal
-          baseClass="add-profile"
           currentTeamId={currentTeamId}
           isPremiumTier={!!isPremiumTier}
           onUpload={onUploadProfile}
@@ -204,7 +207,7 @@ const CustomSettings = ({
           onDelete={onDeleteProfile}
         />
       )}
-      {!!isPremiumTier && !!profileLabelsModalData?.labels?.length && (
+      {isPremiumTier && hasLabels && (
         <ProfileLabelsModal
           baseClass={baseClass}
           profile={profileLabelsModalData}
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/_styles.scss b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/_styles.scss
index 9f6c3eef81..4e56c438b7 100644
--- a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/_styles.scss
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/_styles.scss
@@ -94,136 +94,11 @@
       padding: 28.5px 0;
     }
 
-    &__modal-content-wrap {
-      margin-top: $pad-large;
-
-      .add-profile__file {
-        padding: $pad-medium $pad-large;
-      }
-    }
-
-    &__upload-button {
-      margin-top: 8px;
-      padding: 0;
-    }
-
-    &__file-chooser {
-      display: flex;
-      flex-direction: column;
-      align-items: center;
-      padding-top: $pad-medium;
-
-      input {
-        display: none;
-      }
-
-      &--button-wrap {
-        display: flex;
-        justify-content: center;
-        gap: $pad-small;
-        cursor: pointer;
-        height: 38px;
-        align-items: center;
-      }
-    }
-
-    &__selected-file {
-      display: flex;
-      gap: 16px;
-
-      &--details {
-        display: flex;
-        flex-direction: column;
-
-        &--name {
-          font-size: $x-small;
-          font-weight: $bold;
-        }
-        &--platform {
-          font-size: $xx-small;
-          color: $ui-fleet-black-75;
-        }
-      }
-    }
-
     &__profile-graphic {
       display: flex;
       flex-direction: column;
       align-items: center;
       gap: $pad-small;
     }
-
-    &__button-wrap {
-      display: flex;
-      justify-content: flex-end;
-      padding-top: $pad-medium;
-    }
-
-    &__target {
-      margin: $pad-large 0 $pad-small 0;
-    }
-
-    &__description {
-      margin: $pad-medium 0;
-    }
-
-    &__no-labels {
-      display: flex;
-      height: 187px;
-      flex-direction: column;
-      align-items: center;
-      gap: $pad-small;
-      justify-content: center;
-
-      span {
-        color: $ui-fleet-black-75;
-      }
-    }
-
-    &__checkboxes {
-      display: flex;
-      max-height: 187px;
-      flex-direction: column;
-      border-radius: $border-radius;
-      border: 1px solid $ui-fleet-black-10;
-      overflow-y: auto;
-
-      .loading-spinner {
-        margin: 69.5px auto;
-      }
-    }
-
-    &__label {
-      width: 100%;
-      padding: $pad-small $pad-medium;
-      box-sizing: border-box;
-      display: flex;
-      align-items: center;
-
-      &:not(:last-child) {
-        border-bottom: 1px solid $ui-fleet-black-10;
-      }
-
-      .form-field--checkbox {
-        width: auto;
-      }
-    }
-
-    &__label-name {
-      padding-left: $pad-large;
-    }
-
-    .fleet-checkbox {
-      height: 20px;
-      display: flex;
-      align-items: center;
-
-      &__label {
-        width: 490px;
-        overflow: hidden;
-        text-overflow: ellipsis;
-        white-space: nowrap;
-      }
-    }
   }
 }
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileLabelsModal/ProfileLabelsModal.tsx b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileLabelsModal/ProfileLabelsModal.tsx
index f2fe03944d..4128a5e826 100644
--- a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileLabelsModal/ProfileLabelsModal.tsx
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileLabelsModal/ProfileLabelsModal.tsx
@@ -6,25 +6,42 @@ import InfoBanner from "components/InfoBanner";
 import TooltipWrapper from "components/TooltipWrapper";
 import Icon from "components/Icon";
 
+interface IModalDescriptionProps {
+  baseClass: string;
+  profileName: string;
+  targetType: "includeAll" | "excludeAny";
+}
+
 const ModalDescription = ({
   baseClass,
   profileName,
-}: {
-  baseClass: string;
-  profileName: string;
-}) => (
-  <div className={`${baseClass}__description`}>
-    <b>{profileName}</b> will only be applied to hosts that have all these
-    labels:
-  </div>
-);
+  targetType,
+}: IModalDescriptionProps) => {
+  const targetTypeText =
+    targetType === "includeAll" ? (
+      <>
+        have <b>all</b>
+      </>
+    ) : (
+      <>
+        don&apos;t have <b>any</b>
+      </>
+    );
+
+  return (
+    <div className={`${baseClass}__description`}>
+      <b>{profileName}</b> profile only applies to hosts that {targetTypeText}{" "}
+      of these labels:
+    </div>
+  );
+};
 
 const BrokenLabelWarning = () => (
   <InfoBanner color="yellow">
     <span>
       The configuration profile is{" "}
       <TooltipWrapper
-        tipContent={`It won’t be applied to new hosts because one or more labels are deleted. To apply the profile to new hosts, please delete it and upload a new profile.`}
+        tipContent={`It won't be applied to new hosts because one or more labels are deleted. To apply the profile to new hosts, please delete it and upload a new profile.`}
         underline
       >
         broken
@@ -67,7 +84,14 @@ const ProfileLabelsModal = ({
   profile,
   setModalData,
 }: IProfileLabelsModalProps) => {
-  if (!profile?.labels?.length) {
+  if (!profile) {
+    return null;
+  }
+
+  const { name, labels_include_all, labels_exclude_any } = profile;
+  const labels = labels_include_all || labels_exclude_any;
+
+  if (!labels?.length) {
     // caller ensures this never happens
     return null;
   }
@@ -75,9 +99,13 @@ const ProfileLabelsModal = ({
   return (
     <Modal title="Custom target" onExit={() => setModalData(null)}>
       <div className={`${baseClass}__modal-content-wrap`}>
-        {profile.labels.some((label) => label.broken) && <BrokenLabelWarning />}
-        <ModalDescription baseClass={baseClass} profileName={profile.name} />
-        <LabelsList baseClass={baseClass} labels={profile.labels} />
+        {labels.some((label) => label.broken) && <BrokenLabelWarning />}
+        <ModalDescription
+          baseClass={baseClass}
+          profileName={name}
+          targetType={labels_include_all ? "includeAll" : "excludeAny"}
+        />
+        <LabelsList baseClass={baseClass} labels={labels} />
         <div className="modal-cta-wrap">
           <Button variant="brand" onClick={() => setModalData(null)}>
             Done
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileListItem/ProfileListItem.tsx b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileListItem/ProfileListItem.tsx
index b61ea7c2f0..ea83ddfd5a 100644
--- a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileListItem/ProfileListItem.tsx
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileListItem/ProfileListItem.tsx
@@ -83,7 +83,13 @@ const ProfileListItem = ({
   onDelete,
   setProfileLabelsModalData,
 }: IProfileListItemProps) => {
-  const { created_at, labels, name, platform } = profile;
+  const {
+    created_at,
+    labels_include_all,
+    labels_exclude_any,
+    name,
+    platform,
+  } = profile;
   const subClass = "list-item";
 
   const onClickDownload = async () => {
@@ -95,6 +101,21 @@ const ProfileListItem = ({
     FileSaver.saveAs(file);
   };
 
+  const labels = labels_include_all || labels_exclude_any;
+
+  const renderLabelInfo = () => {
+    if (!isPremium || labels === undefined || labels.length === 0) {
+      return null;
+    }
+
+    return (
+      <div className={`${subClass}__labels`}>
+        {labels?.some((label) => label.broken) && <Icon name="warning" />}
+        <LabelCount className={subClass} count={labels.length} />
+      </div>
+    );
+  };
+
   return (
     <div className={classnames(subClass, baseClass)}>
       <div className={`${subClass}__main-content`}>
@@ -111,14 +132,9 @@ const ProfileListItem = ({
         </div>
       </div>
       <div className={`${subClass}__actions-wrap`}>
-        {isPremium && !!labels?.length && (
-          <div className={`${subClass}__labels`}>
-            {labels?.some((l) => l.broken) && <Icon name="warning" />}
-            <LabelCount className={subClass} count={labels.length} />
-          </div>
-        )}
+        {renderLabelInfo()}
         <div className={`${subClass}__actions`}>
-          {isPremium && !!labels?.length && (
+          {isPremium && labels !== undefined && labels.length && (
             <Button
               className={`${subClass}__action-button`}
               variant="text-icon"
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal.tsx b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/AddProfileModal.tsx
similarity index 71%
rename from frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal.tsx
rename to frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/AddProfileModal.tsx
index b948e9d9dd..88b7e96ed9 100644
--- a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal.tsx
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/AddProfileModal.tsx
@@ -10,6 +10,8 @@ import { ILabelSummary } from "interfaces/label";
 import labelsAPI from "services/entities/labels";
 import mdmAPI from "services/entities/mdm";
 
+// @ts-ignore
+import Dropdown from "components/forms/fields/Dropdown";
 import Button from "components/buttons/Button";
 import Card from "components/Card";
 import Checkbox from "components/forms/fields/Checkbox";
@@ -19,24 +21,28 @@ import Modal from "components/Modal";
 import Radio from "components/forms/fields/Radio";
 import Spinner from "components/Spinner";
 
-import ProfileGraphic from "./AddProfileGraphic";
+import ProfileGraphic from "../AddProfileGraphic";
 
 import {
   DEFAULT_ERROR_MESSAGE,
   getErrorMessage,
   parseFile,
+} from "../../helpers";
+import {
+  CUSTOM_TARGET_OPTIONS,
+  CustomTargetOption,
+  generateLabelKey,
   listNamesFromSelectedLabels,
-} from "../helpers";
+} from "./helpers";
 
-const FileChooser = ({
-  baseClass,
-  isLoading,
-  onFileOpen,
-}: {
-  baseClass: string;
+const baseClass = "add-profile-modal";
+
+interface IFileChooserProps {
   isLoading: boolean;
   onFileOpen: (files: FileList | null) => void;
-}) => (
+}
+
+const FileChooser = ({ isLoading, onFileOpen }: IFileChooserProps) => (
   <div className={`${baseClass}__file-chooser`}>
     <ProfileGraphic baseClass={baseClass} showMessage />
     <Button
@@ -62,19 +68,17 @@ const FileChooser = ({
   </div>
 );
 
-// TODO: if we reuse this one more time, we should consider moving this
-// into FileUploader as a default preview. Currently we have this in
-// AddSoftwareForm.tsx and here.
-const FileDetails = ({
-  baseClass,
-  details: { name, platform },
-}: {
-  baseClass: string;
+interface IFileDetailsProps {
   details: {
     name: string;
     platform: string;
   };
-}) => (
+}
+
+// TODO: if we reuse this one more time, we should consider moving this
+// into FileUploader as a default preview. Currently we have this in
+// AddSoftwareForm.tsx and here.
+const FileDetails = ({ details: { name, platform } }: IFileDetailsProps) => (
   <div className={`${baseClass}__selected-file`}>
     <ProfileGraphic baseClass={baseClass} />
     <div className={`${baseClass}__selected-file--details`}>
@@ -86,15 +90,15 @@ const FileDetails = ({
   </div>
 );
 
-const TargetChooser = ({
-  baseClass,
-  selectedTarget,
-  setSelectedTarget,
-}: {
-  baseClass: string;
+interface ITargetChooserProps {
   selectedTarget: string;
   setSelectedTarget: React.Dispatch<React.SetStateAction<string>>;
-}) => {
+}
+
+const TargetChooser = ({
+  selectedTarget,
+  setSelectedTarget,
+}: ITargetChooserProps) => {
   return (
     <div className={`form-field`}>
       <div className="form-field__label">Target</div>
@@ -120,67 +124,95 @@ const TargetChooser = ({
   );
 };
 
-const LabelChooser = ({
-  baseClass,
-  isError,
-  isLoading,
-  labels,
-  selectedLabels,
-  setSelectedLabels,
-}: {
-  baseClass: string;
+interface ILabelChooserProps {
   isError: boolean;
   isLoading: boolean;
   labels: ILabelSummary[];
   selectedLabels: Record<string, boolean>;
+  customTargetOption: CustomTargetOption;
   setSelectedLabels: React.Dispatch<
     React.SetStateAction<Record<string, boolean>>
   >;
-}) => {
+  onSelectCustomTargetOption: (val: CustomTargetOption) => void;
+}
+
+const LabelChooser = ({
+  isError,
+  isLoading,
+  labels,
+  selectedLabels,
+  customTargetOption,
+  setSelectedLabels,
+  onSelectCustomTargetOption,
+}: ILabelChooserProps) => {
   const updateSelectedLabels = useCallback(
     ({ name, value }: { name: string; value: boolean }) => {
       setSelectedLabels((prevItems) => ({ ...prevItems, [name]: value }));
     },
     [setSelectedLabels]
   );
+
+  const descriptionText =
+    customTargetOption === "labelsIncludeAll" ? (
+      <>
+        Profile will only be applied to hosts that have <b>all</b> these labels:
+      </>
+    ) : (
+      <>
+        Profile will be applied to hosts that don&apos;t have <b>any</b> of
+        these labels:{" "}
+      </>
+    );
+
+  const renderLabels = () => {
+    if (isLoading) {
+      return <Spinner centered={false} />;
+    }
+
+    if (isError) {
+      return <DataError />;
+    }
+
+    if (!labels.length) {
+      return (
+        <div className={`${baseClass}__no-labels`}>
+          <b>No labels exist in Fleet</b>
+          <span>Add labels to target specific hosts.</span>
+        </div>
+      );
+    }
+
+    return labels.map((label) => {
+      return (
+        <div className={`${baseClass}__label`} key={label.name}>
+          <Checkbox
+            className={`${baseClass}__checkbox`}
+            name={label.name}
+            value={!!selectedLabels[label.name]}
+            onChange={updateSelectedLabels}
+            parseTarget
+          />
+          <div className={`${baseClass}__label-name`}>{label.name}</div>
+        </div>
+      );
+    });
+  };
+
   return (
-    <>
-      <div className={`${baseClass}__description`}>
-        Profile will only be applied to hosts that have all these labels:
-      </div>
-      <div className={`${baseClass}__checkboxes`}>
-        {isLoading && <Spinner centered={false} />}
-        {!isLoading && isError && <DataError />}
-        {!isLoading && !isError && !labels.length && (
-          <div className={`${baseClass}__no-labels`}>
-            <b>No labels exist in Fleet</b>
-            <span>Add labels to target specific hosts.</span>
-          </div>
-        )}
-        {!isLoading &&
-          !isError &&
-          !!labels.length &&
-          labels.map((label) => {
-            return (
-              <div className={`${baseClass}__label`} key={label.name}>
-                <Checkbox
-                  className={`${baseClass}__checkbox`}
-                  name={label.name}
-                  value={!!selectedLabels[label.name]}
-                  onChange={updateSelectedLabels}
-                  parseTarget
-                />
-                <div className={`${baseClass}__label-name`}>{label.name}</div>
-              </div>
-            );
-          })}
-      </div>
-    </>
+    <div className={`${baseClass}__custom-label-chooser`}>
+      <Dropdown
+        value={customTargetOption}
+        options={CUSTOM_TARGET_OPTIONS}
+        searchable={false}
+        onChange={onSelectCustomTargetOption}
+      />
+      <div className={`${baseClass}__description`}>{descriptionText}</div>
+      <div className={`${baseClass}__checkboxes`}>{renderLabels()}</div>
+    </div>
   );
 };
 
 interface IAddProfileModalProps {
-  baseClass: string;
   currentTeamId: number;
   isPremiumTier: boolean;
   onUpload: () => void;
@@ -188,7 +220,6 @@ interface IAddProfileModalProps {
 }
 
 const AddProfileModal = ({
-  baseClass,
   currentTeamId,
   isPremiumTier,
   onUpload,
@@ -205,18 +236,20 @@ const AddProfileModal = ({
   const [selectedLabels, setSelectedLabels] = useState<Record<string, boolean>>(
     {}
   );
+  const [
+    customTargetOption,
+    setCustomTargetOption,
+  ] = useState<CustomTargetOption>("labelsIncludeAll");
 
   const fileRef = useRef<File | null>(null);
 
-  // NOTE: labels are not automatically refetched in the current implementation
   const {
     data: labels,
     isLoading: isLoadingLabels,
     isFetching: isFetchingLabels,
     isError: isErrorLabels,
-    // refetch: refetchLabels,
   } = useQuery<ILabelSummary[], Error>(
-    ["custom_labels"], // NOTE: consider adding selectedTarget to the queryKey to refetch labels when target changes
+    ["custom_labels"],
     () =>
       labelsAPI
         .summary()
@@ -246,10 +279,15 @@ const AddProfileModal = ({
 
     setIsLoading(true);
     try {
+      const labelKey = generateLabelKey(
+        selectedTarget,
+        customTargetOption,
+        selectedLabels
+      );
       await mdmAPI.uploadProfile({
         file,
         teamId: currentTeamId,
-        labels: listNamesFromSelectedLabels(selectedLabels),
+        ...labelKey,
       });
       renderFlash("success", "Successfully uploaded!");
       onUpload();
@@ -282,6 +320,10 @@ const AddProfileModal = ({
     }
   };
 
+  const onSelectCustomTargetOption = (val: CustomTargetOption) => {
+    setCustomTargetOption(val);
+  };
+
   return (
     <Modal title="Add profile" onExit={onDone}>
       <>
@@ -291,30 +333,26 @@ const AddProfileModal = ({
           <div className={`${baseClass}__modal-content-wrap`}>
             <Card color="gray" className={`${baseClass}__file`}>
               {!fileDetails ? (
-                <FileChooser
-                  baseClass={baseClass}
-                  isLoading={isLoading}
-                  onFileOpen={onFileOpen}
-                />
+                <FileChooser isLoading={isLoading} onFileOpen={onFileOpen} />
               ) : (
-                <FileDetails baseClass={baseClass} details={fileDetails} />
+                <FileDetails details={fileDetails} />
               )}
             </Card>
             {isPremiumTier && (
               <div className={`${baseClass}__target`}>
                 <TargetChooser
-                  baseClass={baseClass}
                   selectedTarget={selectedTarget}
                   setSelectedTarget={setSelectedTarget}
                 />
                 {selectedTarget === "Custom" && (
                   <LabelChooser
-                    baseClass={baseClass}
+                    customTargetOption={customTargetOption}
                     isError={isErrorLabels}
                     isLoading={isFetchingLabels}
                     labels={labels || []}
                     selectedLabels={selectedLabels}
                     setSelectedLabels={setSelectedLabels}
+                    onSelectCustomTargetOption={onSelectCustomTargetOption}
                   />
                 )}
               </div>
@@ -326,7 +364,6 @@ const AddProfileModal = ({
                 onClick={onFileUpload}
                 isLoading={isLoading}
                 disabled={
-                  // TODO: consider adding tooltip to explain why button is disabled
                   (selectedTarget === "Custom" &&
                     !listNamesFromSelectedLabels(selectedLabels).length) ||
                   !fileDetails
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/_styles.scss b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/_styles.scss
new file mode 100644
index 0000000000..261799fe73
--- /dev/null
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/_styles.scss
@@ -0,0 +1,138 @@
+.add-profile-modal {
+  &__modal-content-wrap {
+    margin-top: $pad-large;
+
+    .add-profile__file {
+      padding: $pad-medium $pad-large;
+    }
+  }
+
+  &__upload-button {
+    margin-top: 8px;
+    padding: 0;
+  }
+
+  &__file-chooser {
+    display: flex;
+    flex-direction: column;
+    align-items: center;
+    padding-top: $pad-medium;
+
+    input {
+      display: none;
+    }
+
+    &--button-wrap {
+      display: flex;
+      justify-content: center;
+      gap: $pad-small;
+      cursor: pointer;
+      height: 38px;
+      align-items: center;
+    }
+  }
+
+  &__selected-file {
+    display: flex;
+    gap: 16px;
+
+    &--details {
+      display: flex;
+      flex-direction: column;
+
+      &--name {
+        font-size: $x-small;
+        font-weight: $bold;
+      }
+
+      &--platform {
+        font-size: $xx-small;
+        color: $ui-fleet-black-75;
+      }
+    }
+  }
+
+  &__profile-graphic {
+    display: flex;
+    flex-direction: column;
+    align-items: center;
+    gap: $pad-small;
+  }
+
+  &__button-wrap {
+    display: flex;
+    justify-content: flex-end;
+    padding-top: $pad-medium;
+  }
+
+  &__target {
+    margin: $pad-large 0;
+  }
+
+  &__custom-label-chooser {
+    margin-top: $pad-medium;
+  }
+
+  &__description {
+    margin: $pad-medium 0;
+  }
+
+  &__no-labels {
+    display: flex;
+    height: 187px;
+    flex-direction: column;
+    align-items: center;
+    gap: $pad-small;
+    justify-content: center;
+
+    span {
+      color: $ui-fleet-black-75;
+    }
+  }
+
+  &__checkboxes {
+    display: flex;
+    max-height: 187px;
+    flex-direction: column;
+    border-radius: $border-radius;
+    border: 1px solid $ui-fleet-black-10;
+    overflow-y: auto;
+
+    .loading-spinner {
+      margin: 69.5px auto;
+    }
+  }
+
+  &__label {
+    width: 100%;
+    padding: $pad-small $pad-medium;
+    box-sizing: border-box;
+    display: flex;
+    align-items: center;
+
+    &:not(:last-child) {
+      border-bottom: 1px solid $ui-fleet-black-10;
+    }
+
+    .form-field--checkbox {
+      width: auto;
+    }
+  }
+
+  &__label-name {
+    padding-left: $pad-large;
+  }
+
+  .fleet-checkbox {
+    height: 20px;
+    display: flex;
+    align-items: center;
+
+    &__label {
+      width: 490px;
+      overflow: hidden;
+      text-overflow: ellipsis;
+      white-space: nowrap;
+    }
+  }
+}
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/helpers.tsx b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/helpers.tsx
new file mode 100644
index 0000000000..e8ff573ece
--- /dev/null
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/helpers.tsx
@@ -0,0 +1,54 @@
+import React from "react";
+
+import { IDropdownOption } from "interfaces/dropdownOption";
+import { snakeCase } from "lodash";
+
+export const CUSTOM_TARGET_OPTIONS: IDropdownOption[] = [
+  {
+    value: "labelsIncludeAll",
+    label: "Include all ",
+    helpText: (
+      <>
+        Profile will only be applied to hosts that have <b>all</b> of these
+        labels{" "}
+      </>
+    ),
+    disabled: false,
+  },
+  {
+    value: "labelsExcludeAny",
+    label: "Exclude all",
+    helpText: (
+      <>
+        Profile will be applied to hosts that don&apos;t have <b>any</b> of
+        these labels{" "}
+      </>
+    ),
+    disabled: false,
+  },
+];
+
+export const listNamesFromSelectedLabels = (dict: Record<string, boolean>) => {
+  return Object.entries(dict).reduce((acc, [labelName, isSelected]) => {
+    if (isSelected) {
+      acc.push(labelName);
+    }
+    return acc;
+  }, [] as string[]);
+};
+
+export type CustomTargetOption = "labelsIncludeAll" | "labelsExcludeAny";
+
+export const generateLabelKey = (
+  target: string,
+  customTargetOption: CustomTargetOption,
+  selectedLabels: Record<string, boolean>
+) => {
+  if (target !== "Custom") {
+    return {};
+  }
+
+  return {
+    [customTargetOption]: listNamesFromSelectedLabels(selectedLabels),
+  };
+};
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/index.ts b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/index.ts
new file mode 100644
index 0000000000..4a6ac9c529
--- /dev/null
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/components/AddProfileModal/index.ts
@@ -0,0 +1 @@
+export { default } from "./AddProfileModal";
diff --git a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/helpers.tsx b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/helpers.tsx
index bef5542e71..62727c9b2f 100644
--- a/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/helpers.tsx
+++ b/frontend/pages/ManageControlsPage/OSSettings/cards/CustomSettings/components/ProfileUploader/helpers.tsx
@@ -2,61 +2,6 @@ import React from "react";
 import { AxiosResponse } from "axios";
 import { IApiError } from "interfaces/errors";
 
-// TODO: mobileconfig parser is a work in progress and not yet used in production
-// https://developer.apple.com/documentation/devicemanagement/configuring_multiple_devices_using_profiles#3234127
-const parseMobileconfig = (file: File): Promise<string> => {
-  return new Promise((resolve, reject) => {
-    const reader = new FileReader();
-    reader.readAsText(file);
-    reader.onerror = (error) => {
-      reject(error);
-    };
-    reader.onabort = (error) => {
-      reject(error);
-    };
-    reader.onload = () => {
-      try {
-        // parse mobile as xml
-        const xmlDoc = new DOMParser().parseFromString(
-          reader.result as string,
-          "text/xml"
-        );
-        // check for any parser errors
-        const parserErrors = xmlDoc.getElementsByTagName("parsererror");
-        if (parserErrors.length > 0) {
-          console.warn("parserErrors", parserErrors);
-          throw new Error("Invalid file: parser error");
-        }
-        // get the top-level object, we assume it is the first `<dict>` element in the `<plist>`
-        // https://developer.apple.com/documentation/devicemanagement/toplevel
-        const tlo = xmlDoc.getElementsByTagName("dict")?.[0];
-        if (tlo?.parentElement?.tagName !== "plist") {
-          throw new Error("Invalid file: missing plist");
-        }
-        // get the payload display name from the top-level object, note that there may be other
-        // `<dict>` elements in the `<plist>`, some of which contain `<key>PayloadDisplayName</key>`
-        // elements, but we ignore those for now
-        const pdnKey = Array.from(tlo.children).find(
-          (child) =>
-            child.tagName === "key" &&
-            child.textContent === "PayloadDisplayName"
-        );
-        const pdnVal =
-          (pdnKey?.nextElementSibling?.tagName === "string" &&
-            pdnKey?.nextElementSibling?.textContent) ||
-          "";
-        // if the payload display name is empty, use the file name
-        const result = pdnVal || file.name;
-        console.log("parseMobileconfig result: ", result);
-        resolve(result);
-      } catch (error) {
-        console.error("error", error);
-        reject(error);
-      }
-    };
-  });
-};
-
 export const parseFile = async (file: File): Promise<[string, string]> => {
   // get the file name and extension
   const nameParts = file.name.split(".");
@@ -68,14 +13,6 @@ export const parseFile = async (file: File): Promise<[string, string]> => {
       return [name, "Windows"];
     }
     case "mobileconfig": {
-      // // TODO: enable this once mobileconfig parser is vetted
-      // try {
-      //   const parsedName = await parseMobileConfig(file);
-      //   return [parsedName, "macOS"];
-      // } catch (e) {
-      //   console.log("error", e);
-      //   return [name, "macOS"];
-      // }
       return [name, "macOS"];
     }
     case "json": {
@@ -87,15 +24,6 @@ export const parseFile = async (file: File): Promise<[string, string]> => {
   }
 };
 
-export const listNamesFromSelectedLabels = (dict: Record<string, boolean>) => {
-  return Object.entries(dict).reduce((acc, [labelName, isSelected]) => {
-    if (isSelected) {
-      acc.push(labelName);
-    }
-    return acc;
-  }, [] as string[]);
-};
-
 export const DEFAULT_ERROR_MESSAGE =
   "Couldn’t add configuration profile. Please try again.";
 
diff --git a/frontend/services/entities/mdm.ts b/frontend/services/entities/mdm.ts
index 7d9c0d9d6a..c1a68c0c5c 100644
--- a/frontend/services/entities/mdm.ts
+++ b/frontend/services/entities/mdm.ts
@@ -1,4 +1,5 @@
 /* eslint-disable @typescript-eslint/explicit-module-boundary-types */
+import { createMockMdmProfile } from "__mocks__/mdmMock";
 import {
   DiskEncryptionStatus,
   IHostMdmProfile,
@@ -45,7 +46,8 @@ export interface IMdmProfilesResponse {
 export interface IUploadProfileApiParams {
   file: File;
   teamId?: number;
-  labels?: string[];
+  labelsIncludeAll?: string[];
+  labelsExcludeAny?: string[];
 }
 
 export const isDDMProfile = (profile: IMdmProfile | IHostMdmProfile) => {
@@ -62,7 +64,7 @@ export interface IAppleSetupEnrollmentProfileResponse {
   name: string;
   uploaded_at: string;
   // enrollment profile is an object with keys found here https://developer.apple.com/documentation/devicemanagement/profile.
-  enrollment_profile: Record<string, any>;
+  enrollment_profile: Record<string, unknown>;
 }
 
 const mdmService = {
@@ -94,10 +96,37 @@ const mdmService = {
       ...params,
     })}`;
 
+    // TODO: disable when API is ready;
+    return new Promise((resolve) => {
+      resolve({
+        profiles: [
+          createMockMdmProfile({
+            labels_exclude_any: [
+              {
+                // id: 1,
+                broken: true,
+                name: "Test Label",
+              },
+              {
+                id: 1,
+                name: "Test Label 2",
+              },
+            ],
+          }),
+        ],
+        meta: { has_next_results: false, has_previous_results: false },
+      });
+    });
+
     return sendRequest("GET", path);
   },
 
-  uploadProfile: ({ file, teamId, labels }: IUploadProfileApiParams) => {
+  uploadProfile: ({
+    file,
+    teamId,
+    labelsIncludeAll,
+    labelsExcludeAny,
+  }: IUploadProfileApiParams) => {
     const { MDM_PROFILES } = endpoints;
 
     const formData = new FormData();
@@ -107,9 +136,15 @@ const mdmService = {
       formData.append("team_id", teamId.toString());
     }
 
-    labels?.forEach((label) => {
-      formData.append("labels", label);
-    });
+    if (labelsIncludeAll || labelsExcludeAny) {
+      const labels = labelsIncludeAll || labelsExcludeAny;
+      const labelKey = labelsIncludeAll
+        ? "labels_include_all"
+        : "labels_exclude_any";
+      labels?.forEach((label) => {
+        formData.append(labelKey, label);
+      });
+    }
 
     return sendRequest("POST", MDM_PROFILES, formData);
   },
@@ -272,7 +307,7 @@ const mdmService = {
     return new Promise((resolve, reject) => {
       reader.addEventListener("load", () => {
         try {
-          const body: Record<string, any> = {
+          const body: Record<string, unknown> = {
             name: file.name,
             enrollment_profile: JSON.parse(reader.result as string),
           };
@@ -284,7 +319,7 @@ const mdmService = {
           );
         } catch {
           // catches invalid JSON
-          reject("Couldn’t upload. The file should include valid JSON.");
+          reject("Couldn't upload. The file should include valid JSON.");
         }
       });
     });