diff --git a/server/src/entities/system-config.entity.ts b/server/src/entities/system-config.entity.ts
index 9b03eb93f3..1ddd6baff3 100644
--- a/server/src/entities/system-config.entity.ts
+++ b/server/src/entities/system-config.entity.ts
@@ -1,117 +1,137 @@
 import { ConcurrentQueueName } from 'src/interfaces/job.interface';
 import { Column, Entity, PrimaryColumn } from 'typeorm';
 
-@Entity('system_config')
-export class SystemConfigEntity<T = SystemConfigValue> {
-  @PrimaryColumn()
-  key!: SystemConfigKey;
+export type SystemConfigValue = string | string[] | number | boolean;
 
-  @Column({ type: 'varchar', nullable: true, transformer: { to: JSON.stringify, from: JSON.parse } })
-  value!: T | T[];
-}
+// https://stackoverflow.com/a/47058976
+// https://stackoverflow.com/a/70692231
+type PathsToStringProps<T> = T extends SystemConfigValue
+  ? []
+  : {
+      [K in keyof T]: [K, ...PathsToStringProps<T[K]>];
+    }[keyof T];
 
-export type SystemConfigValue = string | number | boolean;
+type Join<T extends string[], D extends string> = T extends []
+  ? never
+  : T extends [infer F]
+    ? F
+    : T extends [infer F, ...infer R]
+      ? F extends string
+        ? `${F}${D}${Join<Extract<R, string[]>, D>}`
+        : never
+      : string;
 
 // dot notation matches path in `SystemConfig`
-export enum SystemConfigKey {
-  FFMPEG_CRF = 'ffmpeg.crf',
-  FFMPEG_THREADS = 'ffmpeg.threads',
-  FFMPEG_PRESET = 'ffmpeg.preset',
-  FFMPEG_TARGET_VIDEO_CODEC = 'ffmpeg.targetVideoCodec',
-  FFMPEG_ACCEPTED_VIDEO_CODECS = 'ffmpeg.acceptedVideoCodecs',
-  FFMPEG_TARGET_AUDIO_CODEC = 'ffmpeg.targetAudioCodec',
-  FFMPEG_ACCEPTED_AUDIO_CODECS = 'ffmpeg.acceptedAudioCodecs',
-  FFMPEG_TARGET_RESOLUTION = 'ffmpeg.targetResolution',
-  FFMPEG_MAX_BITRATE = 'ffmpeg.maxBitrate',
-  FFMPEG_BFRAMES = 'ffmpeg.bframes',
-  FFMPEG_REFS = 'ffmpeg.refs',
-  FFMPEG_GOP_SIZE = 'ffmpeg.gopSize',
-  FFMPEG_NPL = 'ffmpeg.npl',
-  FFMPEG_TEMPORAL_AQ = 'ffmpeg.temporalAQ',
-  FFMPEG_CQ_MODE = 'ffmpeg.cqMode',
-  FFMPEG_TWO_PASS = 'ffmpeg.twoPass',
-  FFMPEG_PREFERRED_HW_DEVICE = 'ffmpeg.preferredHwDevice',
-  FFMPEG_TRANSCODE = 'ffmpeg.transcode',
-  FFMPEG_ACCEL = 'ffmpeg.accel',
-  FFMPEG_TONEMAP = 'ffmpeg.tonemap',
+// TODO: migrate to key value per section
+export const SystemConfigKey = {
+  FFMPEG_CRF: 'ffmpeg.crf',
+  FFMPEG_THREADS: 'ffmpeg.threads',
+  FFMPEG_PRESET: 'ffmpeg.preset',
+  FFMPEG_TARGET_VIDEO_CODEC: 'ffmpeg.targetVideoCodec',
+  FFMPEG_ACCEPTED_VIDEO_CODECS: 'ffmpeg.acceptedVideoCodecs',
+  FFMPEG_TARGET_AUDIO_CODEC: 'ffmpeg.targetAudioCodec',
+  FFMPEG_ACCEPTED_AUDIO_CODECS: 'ffmpeg.acceptedAudioCodecs',
+  FFMPEG_TARGET_RESOLUTION: 'ffmpeg.targetResolution',
+  FFMPEG_MAX_BITRATE: 'ffmpeg.maxBitrate',
+  FFMPEG_BFRAMES: 'ffmpeg.bframes',
+  FFMPEG_REFS: 'ffmpeg.refs',
+  FFMPEG_GOP_SIZE: 'ffmpeg.gopSize',
+  FFMPEG_NPL: 'ffmpeg.npl',
+  FFMPEG_TEMPORAL_AQ: 'ffmpeg.temporalAQ',
+  FFMPEG_CQ_MODE: 'ffmpeg.cqMode',
+  FFMPEG_TWO_PASS: 'ffmpeg.twoPass',
+  FFMPEG_PREFERRED_HW_DEVICE: 'ffmpeg.preferredHwDevice',
+  FFMPEG_TRANSCODE: 'ffmpeg.transcode',
+  FFMPEG_ACCEL: 'ffmpeg.accel',
+  FFMPEG_TONEMAP: 'ffmpeg.tonemap',
 
-  JOB_THUMBNAIL_GENERATION_CONCURRENCY = 'job.thumbnailGeneration.concurrency',
-  JOB_METADATA_EXTRACTION_CONCURRENCY = 'job.metadataExtraction.concurrency',
-  JOB_VIDEO_CONVERSION_CONCURRENCY = 'job.videoConversion.concurrency',
-  JOB_FACE_DETECTION_CONCURRENCY = 'job.faceDetection.concurrency',
-  JOB_CLIP_ENCODING_CONCURRENCY = 'job.smartSearch.concurrency',
-  JOB_BACKGROUND_TASK_CONCURRENCY = 'job.backgroundTask.concurrency',
-  JOB_STORAGE_TEMPLATE_MIGRATION_CONCURRENCY = 'job.storageTemplateMigration.concurrency',
-  JOB_SEARCH_CONCURRENCY = 'job.search.concurrency',
-  JOB_SIDECAR_CONCURRENCY = 'job.sidecar.concurrency',
-  JOB_LIBRARY_CONCURRENCY = 'job.library.concurrency',
-  JOB_MIGRATION_CONCURRENCY = 'job.migration.concurrency',
+  JOB_THUMBNAIL_GENERATION_CONCURRENCY: 'job.thumbnailGeneration.concurrency',
+  JOB_METADATA_EXTRACTION_CONCURRENCY: 'job.metadataExtraction.concurrency',
+  JOB_VIDEO_CONVERSION_CONCURRENCY: 'job.videoConversion.concurrency',
+  JOB_FACE_DETECTION_CONCURRENCY: 'job.faceDetection.concurrency',
+  JOB_CLIP_ENCODING_CONCURRENCY: 'job.smartSearch.concurrency',
+  JOB_BACKGROUND_TASK_CONCURRENCY: 'job.backgroundTask.concurrency',
+  JOB_SEARCH_CONCURRENCY: 'job.search.concurrency',
+  JOB_SIDECAR_CONCURRENCY: 'job.sidecar.concurrency',
+  JOB_LIBRARY_CONCURRENCY: 'job.library.concurrency',
+  JOB_MIGRATION_CONCURRENCY: 'job.migration.concurrency',
 
-  LIBRARY_SCAN_ENABLED = 'library.scan.enabled',
-  LIBRARY_SCAN_CRON_EXPRESSION = 'library.scan.cronExpression',
+  LIBRARY_SCAN_ENABLED: 'library.scan.enabled',
+  LIBRARY_SCAN_CRON_EXPRESSION: 'library.scan.cronExpression',
 
-  LIBRARY_WATCH_ENABLED = 'library.watch.enabled',
+  LIBRARY_WATCH_ENABLED: 'library.watch.enabled',
 
-  LOGGING_ENABLED = 'logging.enabled',
-  LOGGING_LEVEL = 'logging.level',
+  LOGGING_ENABLED: 'logging.enabled',
+  LOGGING_LEVEL: 'logging.level',
 
-  MACHINE_LEARNING_ENABLED = 'machineLearning.enabled',
-  MACHINE_LEARNING_URL = 'machineLearning.url',
+  MACHINE_LEARNING_ENABLED: 'machineLearning.enabled',
+  MACHINE_LEARNING_URL: 'machineLearning.url',
 
-  MACHINE_LEARNING_CLIP_ENABLED = 'machineLearning.clip.enabled',
-  MACHINE_LEARNING_CLIP_MODEL_NAME = 'machineLearning.clip.modelName',
+  MACHINE_LEARNING_CLIP_ENABLED: 'machineLearning.clip.enabled',
+  MACHINE_LEARNING_CLIP_MODEL_NAME: 'machineLearning.clip.modelName',
 
-  MACHINE_LEARNING_FACIAL_RECOGNITION_ENABLED = 'machineLearning.facialRecognition.enabled',
-  MACHINE_LEARNING_FACIAL_RECOGNITION_MODEL_NAME = 'machineLearning.facialRecognition.modelName',
-  MACHINE_LEARNING_FACIAL_RECOGNITION_MIN_SCORE = 'machineLearning.facialRecognition.minScore',
-  MACHINE_LEARNING_FACIAL_RECOGNITION_MAX_DISTANCE = 'machineLearning.facialRecognition.maxDistance',
-  MACHINE_LEARNING_FACIAL_RECOGNITION_MIN_FACES = 'machineLearning.facialRecognition.minFaces',
+  MACHINE_LEARNING_FACIAL_RECOGNITION_ENABLED: 'machineLearning.facialRecognition.enabled',
+  MACHINE_LEARNING_FACIAL_RECOGNITION_MODEL_NAME: 'machineLearning.facialRecognition.modelName',
+  MACHINE_LEARNING_FACIAL_RECOGNITION_MIN_SCORE: 'machineLearning.facialRecognition.minScore',
+  MACHINE_LEARNING_FACIAL_RECOGNITION_MAX_DISTANCE: 'machineLearning.facialRecognition.maxDistance',
+  MACHINE_LEARNING_FACIAL_RECOGNITION_MIN_FACES: 'machineLearning.facialRecognition.minFaces',
 
-  MAP_ENABLED = 'map.enabled',
-  MAP_LIGHT_STYLE = 'map.lightStyle',
-  MAP_DARK_STYLE = 'map.darkStyle',
+  MAP_ENABLED: 'map.enabled',
+  MAP_LIGHT_STYLE: 'map.lightStyle',
+  MAP_DARK_STYLE: 'map.darkStyle',
 
-  REVERSE_GEOCODING_ENABLED = 'reverseGeocoding.enabled',
+  REVERSE_GEOCODING_ENABLED: 'reverseGeocoding.enabled',
 
-  NEW_VERSION_CHECK_ENABLED = 'newVersionCheck.enabled',
+  NEW_VERSION_CHECK_ENABLED: 'newVersionCheck.enabled',
 
-  OAUTH_AUTO_LAUNCH = 'oauth.autoLaunch',
-  OAUTH_AUTO_REGISTER = 'oauth.autoRegister',
-  OAUTH_BUTTON_TEXT = 'oauth.buttonText',
-  OAUTH_CLIENT_ID = 'oauth.clientId',
-  OAUTH_CLIENT_SECRET = 'oauth.clientSecret',
-  OAUTH_DEFAULT_STORAGE_QUOTA = 'oauth.defaultStorageQuota',
-  OAUTH_ENABLED = 'oauth.enabled',
-  OAUTH_ISSUER_URL = 'oauth.issuerUrl',
-  OAUTH_MOBILE_OVERRIDE_ENABLED = 'oauth.mobileOverrideEnabled',
-  OAUTH_MOBILE_REDIRECT_URI = 'oauth.mobileRedirectUri',
-  OAUTH_SCOPE = 'oauth.scope',
-  OAUTH_SIGNING_ALGORITHM = 'oauth.signingAlgorithm',
-  OAUTH_STORAGE_LABEL_CLAIM = 'oauth.storageLabelClaim',
-  OAUTH_STORAGE_QUOTA_CLAIM = 'oauth.storageQuotaClaim',
+  OAUTH_AUTO_LAUNCH: 'oauth.autoLaunch',
+  OAUTH_AUTO_REGISTER: 'oauth.autoRegister',
+  OAUTH_BUTTON_TEXT: 'oauth.buttonText',
+  OAUTH_CLIENT_ID: 'oauth.clientId',
+  OAUTH_CLIENT_SECRET: 'oauth.clientSecret',
+  OAUTH_DEFAULT_STORAGE_QUOTA: 'oauth.defaultStorageQuota',
+  OAUTH_ENABLED: 'oauth.enabled',
+  OAUTH_ISSUER_URL: 'oauth.issuerUrl',
+  OAUTH_MOBILE_OVERRIDE_ENABLED: 'oauth.mobileOverrideEnabled',
+  OAUTH_MOBILE_REDIRECT_URI: 'oauth.mobileRedirectUri',
+  OAUTH_SCOPE: 'oauth.scope',
+  OAUTH_SIGNING_ALGORITHM: 'oauth.signingAlgorithm',
+  OAUTH_STORAGE_LABEL_CLAIM: 'oauth.storageLabelClaim',
+  OAUTH_STORAGE_QUOTA_CLAIM: 'oauth.storageQuotaClaim',
 
-  PASSWORD_LOGIN_ENABLED = 'passwordLogin.enabled',
+  PASSWORD_LOGIN_ENABLED: 'passwordLogin.enabled',
 
-  SERVER_EXTERNAL_DOMAIN = 'server.externalDomain',
-  SERVER_LOGIN_PAGE_MESSAGE = 'server.loginPageMessage',
+  SERVER_EXTERNAL_DOMAIN: 'server.externalDomain',
+  SERVER_LOGIN_PAGE_MESSAGE: 'server.loginPageMessage',
 
-  STORAGE_TEMPLATE_ENABLED = 'storageTemplate.enabled',
-  STORAGE_TEMPLATE_HASH_VERIFICATION_ENABLED = 'storageTemplate.hashVerificationEnabled',
-  STORAGE_TEMPLATE = 'storageTemplate.template',
+  STORAGE_TEMPLATE_ENABLED: 'storageTemplate.enabled',
+  STORAGE_TEMPLATE_HASH_VERIFICATION_ENABLED: 'storageTemplate.hashVerificationEnabled',
+  STORAGE_TEMPLATE: 'storageTemplate.template',
 
-  IMAGE_THUMBNAIL_FORMAT = 'image.thumbnailFormat',
-  IMAGE_THUMBNAIL_SIZE = 'image.thumbnailSize',
-  IMAGE_PREVIEW_FORMAT = 'image.previewFormat',
-  IMAGE_PREVIEW_SIZE = 'image.previewSize',
-  IMAGE_QUALITY = 'image.quality',
-  IMAGE_COLORSPACE = 'image.colorspace',
+  IMAGE_THUMBNAIL_FORMAT: 'image.thumbnailFormat',
+  IMAGE_THUMBNAIL_SIZE: 'image.thumbnailSize',
+  IMAGE_PREVIEW_FORMAT: 'image.previewFormat',
+  IMAGE_PREVIEW_SIZE: 'image.previewSize',
+  IMAGE_QUALITY: 'image.quality',
+  IMAGE_COLORSPACE: 'image.colorspace',
 
-  TRASH_ENABLED = 'trash.enabled',
-  TRASH_DAYS = 'trash.days',
+  TRASH_ENABLED: 'trash.enabled',
+  TRASH_DAYS: 'trash.days',
 
-  THEME_CUSTOM_CSS = 'theme.customCss',
+  THEME_CUSTOM_CSS: 'theme.customCss',
 
-  USER_DELETE_DELAY = 'user.deleteDelay',
+  USER_DELETE_DELAY: 'user.deleteDelay',
+} as const satisfies Record<string, Join<PathsToStringProps<SystemConfig>, '.'>>;
+
+export type SystemConfigKeyPaths = (typeof SystemConfigKey)[keyof typeof SystemConfigKey];
+
+@Entity('system_config')
+export class SystemConfigEntity<T = SystemConfigValue> {
+  @PrimaryColumn({ type: 'varchar' })
+  key!: SystemConfigKeyPaths;
+
+  @Column({ type: 'varchar', nullable: true, transformer: { to: JSON.stringify, from: JSON.parse } })
+  value!: T;
 }
 
 export enum TranscodePolicy {
diff --git a/server/src/services/job.service.spec.ts b/server/src/services/job.service.spec.ts
index ac0e502ae8..c141586dbe 100644
--- a/server/src/services/job.service.spec.ts
+++ b/server/src/services/job.service.spec.ts
@@ -1,6 +1,6 @@
 import { BadRequestException } from '@nestjs/common';
 import { FeatureFlag, SystemConfigCore } from 'src/cores/system-config.core';
-import { SystemConfig, SystemConfigKey } from 'src/entities/system-config.entity';
+import { SystemConfig, SystemConfigKey, SystemConfigKeyPaths } from 'src/entities/system-config.entity';
 import { IAssetRepository } from 'src/interfaces/asset.interface';
 import { IEventRepository } from 'src/interfaces/event.interface';
 import {
@@ -360,7 +360,7 @@ describe(JobService.name, () => {
       });
     }
 
-    const featureTests: Array<{ queue: QueueName; feature: FeatureFlag; configKey: SystemConfigKey }> = [
+    const featureTests: Array<{ queue: QueueName; feature: FeatureFlag; configKey: SystemConfigKeyPaths }> = [
       {
         queue: QueueName.SMART_SEARCH,
         feature: FeatureFlag.SMART_SEARCH,