diff --git a/app/components/files/index.ts b/app/components/files/index.ts
index 2f034ab4b7..5945f9b62f 100644
--- a/app/components/files/index.ts
+++ b/app/components/files/index.ts
@@ -3,11 +3,11 @@
 
 import {withDatabase} from '@nozbe/watermelondb/DatabaseProvider';
 import withObservables from '@nozbe/with-observables';
-import {combineLatest, of as of$, from as from$} from 'rxjs';
-import {map, switchMap} from 'rxjs/operators';
+import {of as of$, from as from$} from 'rxjs';
+import {switchMap} from 'rxjs/operators';
 
 import {queryFilesForPost} from '@queries/servers/file';
-import {observeConfigBooleanValue, observeLicense} from '@queries/servers/system';
+import {observeCanDownloadFiles, observeConfigBooleanValue} from '@queries/servers/system';
 import {fileExists} from '@utils/file';
 
 import Files from './files';
@@ -37,23 +37,14 @@ const filesLocalPathValidation = async (files: FileModel[], authorId: string) =>
 };
 
 const enhance = withObservables(['post'], ({database, post}: EnhanceProps) => {
-    const enableMobileFileDownload = observeConfigBooleanValue(database, 'EnableMobileFileDownload');
     const publicLinkEnabled = observeConfigBooleanValue(database, 'EnablePublicLink');
 
-    const complianceDisabled = observeLicense(database).pipe(
-        switchMap((lcs) => of$(lcs?.IsLicensed === 'false' || lcs?.Compliance === 'false')),
-    );
-
-    const canDownloadFiles = combineLatest([enableMobileFileDownload, complianceDisabled]).pipe(
-        map(([download, compliance]) => compliance || download),
-    );
-
     const filesInfo = queryFilesForPost(database, post.id).observeWithColumns(['local_path']).pipe(
         switchMap((fs) => from$(filesLocalPathValidation(fs, post.userId))),
     );
 
     return {
-        canDownloadFiles,
+        canDownloadFiles: observeCanDownloadFiles(database),
         postId: of$(post.id),
         publicLinkEnabled,
         filesInfo,
diff --git a/app/queries/servers/system.test.ts b/app/queries/servers/system.test.ts
new file mode 100644
index 0000000000..63ff693b3d
--- /dev/null
+++ b/app/queries/servers/system.test.ts
@@ -0,0 +1,254 @@
+// Copyright (c) 2015-present Mattermost, Inc. All Rights Reserved.
+// See LICENSE.txt for license information.
+
+import {SYSTEM_IDENTIFIERS} from '@constants/database';
+import DatabaseManager from '@database/manager';
+
+import {observeCanDownloadFiles, observeCanUploadFiles} from './system';
+
+import type ServerDataOperator from '@database/operator/server_data_operator';
+import type {Database} from '@nozbe/watermelondb';
+
+describe('observeCanUploadFiles', () => {
+    const serverUrl = 'baseHandler.test.com';
+    let database: Database;
+    let operator: ServerDataOperator;
+    beforeEach(async () => {
+        await DatabaseManager.init([serverUrl]);
+        const serverDatabaseAndOperator = DatabaseManager.getServerDatabaseAndOperator(serverUrl);
+        database = serverDatabaseAndOperator.database;
+        operator = serverDatabaseAndOperator.operator;
+    });
+    afterEach(async () => {
+        await DatabaseManager.destroyServerDatabase(serverUrl);
+    });
+
+    it('should return true if no file attachment config value', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableMobileFileUpload', value: 'true'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            observeCanUploadFiles(database).subscribe((data) => {
+                if (data === true) {
+                    done();
+                } else {
+                    done.fail();
+                }
+            });
+        });
+    }, 1500);
+
+    it('should return false if file attachment config value is false', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'false'}, {id: 'EnableMobileFileUpload', value: 'true'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            observeCanUploadFiles(database).subscribe((data) => {
+                if (data === false) {
+                    done();
+                } else {
+                    done.fail();
+                }
+            });
+        });
+    }, 1500);
+
+    it('should return true if file attachment config value is true and there is no license', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'true'}, {id: 'EnableMobileFileUpload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            observeCanUploadFiles(database).subscribe((data) => {
+                if (data === true) {
+                    done();
+                } else {
+                    done.fail();
+                }
+            });
+        });
+    }, 1500);
+
+    it('should return true if file attachment config value is true and server is not licensed', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'true'}, {id: 'EnableMobileFileUpload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {isLicensed: false}}], prepareRecordsOnly: false}).then(() => {
+                observeCanUploadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if file attachment config value is true and server is licensed, but no compliance is set', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'true'}, {id: 'EnableMobileFileUpload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanUploadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if file attachment config value is true and server is licensed, but compliance is set to false', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'true'}, {id: 'EnableMobileFileUpload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'false'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanUploadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if file attachment config value is true and server is licensed and compliance is set to true, but EnableMobileFileUpload is not set', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'true'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'true'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanUploadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return false if file attachment config value is true and server is licensed and compliance is set to true, but EnableMobileFileUpload is set to false', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'true'}, {id: 'EnableMobileFileUpload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'true'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanUploadFiles(database).subscribe((data) => {
+                    if (data === false) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if file attachment config value is true and server is licensed and compliance is set to true, but EnableMobileFileUpload is set to true', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableFileAttachments', value: 'true'}, {id: 'EnableMobileFileUpload', value: 'true'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'true'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanUploadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+});
+
+describe('observeCanDownloadFiles', () => {
+    const serverUrl = 'baseHandler.test.com';
+    let database: Database;
+    let operator: ServerDataOperator;
+    beforeEach(async () => {
+        await DatabaseManager.init([serverUrl]);
+        const serverDatabaseAndOperator = DatabaseManager.getServerDatabaseAndOperator(serverUrl);
+        database = serverDatabaseAndOperator.database;
+        operator = serverDatabaseAndOperator.operator;
+    });
+    afterEach(async () => {
+        await DatabaseManager.destroyServerDatabase(serverUrl);
+    });
+
+    it('should return true if there is no license', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableMobileFileDownload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            observeCanDownloadFiles(database).subscribe((data) => {
+                if (data === true) {
+                    done();
+                } else {
+                    done.fail();
+                }
+            });
+        });
+    }, 1500);
+
+    it('should return true if server is not licensed', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableMobileFileDownload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {isLicensed: false}}], prepareRecordsOnly: false}).then(() => {
+                observeCanDownloadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if server is licensed, but no compliance is set', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableMobileFileDownload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanDownloadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if server is licensed, but compliance is set to false', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableMobileFileDownload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'false'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanDownloadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if is licensed and compliance is set to true, but EnableMobileFileDownload is not set', (done) => {
+        operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'true'}}], prepareRecordsOnly: false}).then(() => {
+            observeCanDownloadFiles(database).subscribe((data) => {
+                if (data === true) {
+                    done();
+                } else {
+                    done.fail();
+                }
+            });
+        });
+    }, 1500);
+
+    it('should return false if server is licensed and compliance is set to true, but EnableMobileFileDownload is set to false', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableMobileFileDownload', value: 'false'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'true'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanDownloadFiles(database).subscribe((data) => {
+                    if (data === false) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+
+    it('should return true if server is licensed and compliance is set to true, but EnableMobileFileDownload is set to true', (done) => {
+        operator.handleConfigs({configs: [{id: 'EnableMobileFileDownload', value: 'true'}], prepareRecordsOnly: false, configsToDelete: []}).then(() => {
+            operator.handleSystem({systems: [{id: SYSTEM_IDENTIFIERS.LICENSE, value: {IsLicensed: 'true', Compliance: 'true'}}], prepareRecordsOnly: false}).then(() => {
+                observeCanDownloadFiles(database).subscribe((data) => {
+                    if (data === true) {
+                        done();
+                    } else {
+                        done.fail();
+                    }
+                });
+            });
+        });
+    }, 1500);
+});
diff --git a/app/queries/servers/system.ts b/app/queries/servers/system.ts
index e17bc40cce..76cfa9ae79 100644
--- a/app/queries/servers/system.ts
+++ b/app/queries/servers/system.ts
@@ -226,9 +226,9 @@ export const observeIsCustomStatusExpirySupported = (database: Database) => {
     );
 };
 
-export const observeConfigBooleanValue = (database: Database, key: keyof ClientConfig) => {
+export const observeConfigBooleanValue = (database: Database, key: keyof ClientConfig, defaultValue = false) => {
     return observeConfigValue(database, key).pipe(
-        switchMap((v) => of$(v === 'true')),
+        switchMap((v) => of$(v ? v === 'true' : defaultValue)),
         distinctUntilChanged(),
     );
 };
@@ -511,16 +511,24 @@ export const observeLastDismissedAnnouncement = (database: Database) => {
 };
 
 export const observeCanUploadFiles = (database: Database) => {
-    const enableFileAttachments = observeConfigBooleanValue(database, 'EnableFileAttachments');
-    const enableMobileFileUpload = observeConfigBooleanValue(database, 'EnableMobileFileUpload');
+    const enableFileAttachments = observeConfigBooleanValue(database, 'EnableFileAttachments', true);
+    const enableMobileFileUpload = observeConfigBooleanValue(database, 'EnableMobileFileUpload', true);
     const license = observeLicense(database);
 
     return combineLatest([enableFileAttachments, enableMobileFileUpload, license]).pipe(
         switchMap(([efa, emfu, l]) => of$(
-            efa ||
-                (l?.IsLicensed !== 'true' && l?.Compliance !== 'true' && emfu),
-        ),
-        ),
+            efa &&
+                (l?.IsLicensed !== 'true' || l?.Compliance !== 'true' || emfu),
+        )),
+    );
+};
+
+export const observeCanDownloadFiles = (database: Database) => {
+    const enableMobileFileDownload = observeConfigBooleanValue(database, 'EnableMobileFileDownload', true);
+    const license = observeLicense(database);
+
+    return combineLatest([enableMobileFileDownload, license]).pipe(
+        switchMap(([emfd, l]) => of$((l?.IsLicensed !== 'true' || l?.Compliance !== 'true' || emfd))),
     );
 };
 
diff --git a/app/screens/gallery/document_renderer/index.ts b/app/screens/gallery/document_renderer/index.ts
index df8ffefa02..e54326142b 100644
--- a/app/screens/gallery/document_renderer/index.ts
+++ b/app/screens/gallery/document_renderer/index.ts
@@ -3,26 +3,16 @@
 
 import {withDatabase} from '@nozbe/watermelondb/DatabaseProvider';
 import withObservables from '@nozbe/with-observables';
-import {combineLatest, of as of$} from 'rxjs';
-import {switchMap} from 'rxjs/operators';
 
-import {observeConfigBooleanValue, observeLicense} from '@queries/servers/system';
+import {observeCanDownloadFiles} from '@queries/servers/system';
 
 import DocumentRenderer from './document_renderer';
 
 import type {WithDatabaseArgs} from '@typings/database/database';
 
 const enhanced = withObservables([], ({database}: WithDatabaseArgs) => {
-    const enableMobileFileDownload = observeConfigBooleanValue(database, 'EnableMobileFileDownload');
-    const complianceDisabled = observeLicense(database).pipe(
-        switchMap((lcs) => of$(lcs?.IsLicensed === 'false' || lcs?.Compliance === 'false')),
-    );
-    const canDownloadFiles = combineLatest([enableMobileFileDownload, complianceDisabled]).pipe(
-        switchMap(([download, compliance]) => of$(compliance || download)),
-    );
-
     return {
-        canDownloadFiles,
+        canDownloadFiles: observeCanDownloadFiles(database),
     };
 });
 
diff --git a/app/screens/gallery/footer/index.ts b/app/screens/gallery/footer/index.ts
index a7561289a8..42f86358f2 100644
--- a/app/screens/gallery/footer/index.ts
+++ b/app/screens/gallery/footer/index.ts
@@ -9,7 +9,7 @@ import {switchMap} from 'rxjs/operators';
 import {General} from '@constants';
 import {observeChannel} from '@queries/servers/channel';
 import {observePost} from '@queries/servers/post';
-import {observeConfigBooleanValue, observeCurrentChannelId, observeCurrentUserId, observeLicense} from '@queries/servers/system';
+import {observeCanDownloadFiles, observeConfigBooleanValue, observeCurrentChannelId, observeCurrentUserId} from '@queries/servers/system';
 import {observeTeammateNameDisplay, observeUser} from '@queries/servers/user';
 
 import Footer from './footer';
@@ -27,7 +27,6 @@ const enhanced = withObservables(['item'], ({database, item}: FooterProps) => {
     const currentChannelId = observeCurrentChannelId(database);
     const currentUserId = observeCurrentUserId(database);
 
-    const license = observeLicense(database);
     const teammateNameDisplay = observeTeammateNameDisplay(database);
 
     const author = post.pipe(
@@ -50,17 +49,12 @@ const enhanced = withObservables(['item'], ({database, item}: FooterProps) => {
     const enablePostUsernameOverride = observeConfigBooleanValue(database, 'EnablePostUsernameOverride');
     const enablePostIconOverride = observeConfigBooleanValue(database, 'EnablePostIconOverride');
     const enablePublicLink = observeConfigBooleanValue(database, 'EnablePublicLink');
-    const enableMobileFileDownload = observeConfigBooleanValue(database, 'EnableMobileFileDownload');
-    const complianceDisabled = license.pipe(switchMap((l) => of$(l?.IsLicensed === 'false' || l?.Compliance === 'false')));
-    const canDownloadFiles = combineLatest([enableMobileFileDownload, complianceDisabled]).pipe(
-        switchMap(([download, compliance]) => of$(compliance || download)),
-    );
     const channelName = channel.pipe(switchMap((c: ChannelModel) => of$(c.displayName)));
     const isDirectChannel = channel.pipe(switchMap((c: ChannelModel) => of$(c.type === General.DM_CHANNEL)));
 
     return {
         author,
-        canDownloadFiles,
+        canDownloadFiles: observeCanDownloadFiles(database),
         channelName,
         currentUserId,
         enablePostIconOverride,
diff --git a/app/screens/home/search/results/file_options/option_menus/index.tsx b/app/screens/home/search/results/file_options/option_menus/index.tsx
index 117a2b9b04..5412631b6f 100644
--- a/app/screens/home/search/results/file_options/option_menus/index.tsx
+++ b/app/screens/home/search/results/file_options/option_menus/index.tsx
@@ -4,28 +4,16 @@
 import {withDatabase} from '@nozbe/watermelondb/DatabaseProvider';
 import withObservables from '@nozbe/with-observables';
 import compose from 'lodash/fp/compose';
-import {combineLatest, of as of$} from 'rxjs';
-import {map, switchMap} from 'rxjs/operators';
 
-import {observeLicense, observeConfigBooleanValue} from '@queries/servers/system';
+import {observeConfigBooleanValue, observeCanDownloadFiles} from '@queries/servers/system';
 
 import OptionMenus from './option_menus';
 
 import type {WithDatabaseArgs} from '@typings/database/database';
 
 const enhance = withObservables([], ({database}: WithDatabaseArgs) => {
-    const enableMobileFileDownload = observeConfigBooleanValue(database, 'EnableMobileFileDownload');
-
-    const complianceDisabled = observeLicense(database).pipe(
-        switchMap((lcs) => of$(lcs?.IsLicensed === 'false' || lcs?.Compliance === 'false')),
-    );
-
-    const canDownloadFiles = combineLatest([enableMobileFileDownload, complianceDisabled]).pipe(
-        map(([download, compliance]) => compliance || download),
-    );
-
     return {
-        canDownloadFiles,
+        canDownloadFiles: observeCanDownloadFiles(database),
         enablePublicLink: observeConfigBooleanValue(database, 'EnablePublicLink'),
     };
 });
diff --git a/app/screens/home/search/results/index.tsx b/app/screens/home/search/results/index.tsx
index 2e0a9167c2..39d3eccb69 100644
--- a/app/screens/home/search/results/index.tsx
+++ b/app/screens/home/search/results/index.tsx
@@ -4,12 +4,12 @@
 import {withDatabase} from '@nozbe/watermelondb/DatabaseProvider';
 import withObservables from '@nozbe/with-observables';
 import compose from 'lodash/fp/compose';
-import {combineLatest, of as of$} from 'rxjs';
-import {map, switchMap} from 'rxjs/operators';
+import {of as of$} from 'rxjs';
+import {switchMap} from 'rxjs/operators';
 
 import {queryChannelsById} from '@queries/servers/channel';
 import {queryAllCustomEmojis} from '@queries/servers/custom_emoji';
-import {observeLicense, observeConfigBooleanValue} from '@queries/servers/system';
+import {observeConfigBooleanValue, observeCanDownloadFiles} from '@queries/servers/system';
 import {observeCurrentUser} from '@queries/servers/user';
 import {mapCustomEmojiNames} from '@utils/emoji/helpers';
 import {getTimezone} from '@utils/user';
@@ -26,16 +26,6 @@ const enhance = withObservables(['fileChannelIds'], ({database, fileChannelIds}:
     const fileChannels = queryChannelsById(database, fileChannelIds).observeWithColumns(['displayName']);
     const currentUser = observeCurrentUser(database);
 
-    const enableMobileFileDownload = observeConfigBooleanValue(database, 'EnableMobileFileDownload');
-
-    const complianceDisabled = observeLicense(database).pipe(
-        switchMap((lcs) => of$(lcs?.IsLicensed === 'false' || lcs?.Compliance === 'false')),
-    );
-
-    const canDownloadFiles = combineLatest([enableMobileFileDownload, complianceDisabled]).pipe(
-        map(([download, compliance]) => compliance || download),
-    );
-
     return {
         appsEnabled: observeConfigBooleanValue(database, 'FeatureFlagAppsEnabled'),
         currentTimezone: currentUser.pipe((switchMap((user) => of$(getTimezone(user?.timezone))))),
@@ -44,7 +34,7 @@ const enhance = withObservables(['fileChannelIds'], ({database, fileChannelIds}:
         ),
         isTimezoneEnabled: observeConfigBooleanValue(database, 'ExperimentalTimezone'),
         fileChannels,
-        canDownloadFiles,
+        canDownloadFiles: observeCanDownloadFiles(database),
         publicLinkEnabled: observeConfigBooleanValue(database, 'EnablePublicLink'),
     };
 });