diff --git a/server/core/lib/schedulers/video-channel-sync-latest-scheduler.ts b/server/core/lib/schedulers/video-channel-sync-latest-scheduler.ts
index 2a3ad18b1..2273265ac 100644
--- a/server/core/lib/schedulers/video-channel-sync-latest-scheduler.ts
+++ b/server/core/lib/schedulers/video-channel-sync-latest-scheduler.ts
@@ -29,17 +29,22 @@ export class VideoChannelSyncLatestScheduler extends AbstractScheduler {
 
       logger.info(
         'Creating video import jobs for "%s" sync with external channel "%s"',
-        channel.Actor.preferredUsername, sync.externalChannelUrl
+        channel.Actor.preferredUsername,
+        sync.externalChannelUrl
       )
 
-      const onlyAfter = sync.lastSyncAt || sync.createdAt
+      // We can't rely on publication date for playlist elements
+      // For example, an old video may have been added to a playlist since the last sync
+      const skipPublishedBefore = this.isPlaylistUrl(sync.externalChannelUrl)
+        ? undefined
+        : sync.lastSyncAt || sync.createdAt
 
       await synchronizeChannel({
         channel,
         externalChannelUrl: sync.externalChannelUrl,
         videosCountLimit: CONFIG.IMPORT.VIDEO_CHANNEL_SYNCHRONIZATION.VIDEOS_LIMIT_PER_SYNCHRONIZATION,
         channelSync: sync,
-        onlyAfter
+        skipPublishedBefore
       })
     }
   }
@@ -47,4 +52,14 @@ export class VideoChannelSyncLatestScheduler extends AbstractScheduler {
   static get Instance () {
     return this.instance || (this.instance = new this())
   }
+
+  private isPlaylistUrl (url: string): boolean {
+    const parsed = new URL(url)
+    const pathname = parsed.pathname.toLowerCase()
+
+    return pathname.startsWith('/playlist/') || // Dailymotion playlist
+      pathname.startsWith('/showcase/') || // Vimeo playlist
+      pathname.startsWith('/playlist?') || // YouTube playlist
+      pathname.startsWith('/w/p/') // PeerTube playlist
+  }
 }
diff --git a/server/core/lib/sync-channel.ts b/server/core/lib/sync-channel.ts
index d83a26043..ad642e481 100644
--- a/server/core/lib/sync-channel.ts
+++ b/server/core/lib/sync-channel.ts
@@ -16,9 +16,9 @@ export async function synchronizeChannel (options: {
   externalChannelUrl: string
   videosCountLimit: number
   channelSync?: MChannelSync
-  onlyAfter?: Date
+  skipPublishedBefore?: Date
 }) {
-  const { channel, externalChannelUrl, videosCountLimit, onlyAfter, channelSync } = options
+  const { channel, externalChannelUrl, videosCountLimit, skipPublishedBefore, channelSync } = options
 
   if (channelSync) {
     channelSync.state = VideoChannelSyncState.PROCESSING
@@ -58,7 +58,7 @@ export async function synchronizeChannel (options: {
       logger.debug(`Import candidate: ${targetUrl}`, lTags())
 
       try {
-        if (await skipImport({ channel, channelSync, targetUrl, onlyAfter })) continue
+        if (await skipImport({ channel, channelSync, targetUrl, skipPublishedBefore })) continue
 
         const { job } = await buildYoutubeDLImport({
           user,
@@ -98,9 +98,9 @@ async function skipImport (options: {
   channel: MChannelAccountDefault
   channelSync: MChannelSync
   targetUrl: string
-  onlyAfter?: Date
+  skipPublishedBefore?: Date
 }) {
-  const { channel, channelSync, targetUrl, onlyAfter } = options
+  const { channel, channelSync, targetUrl, skipPublishedBefore } = options
 
   if (await VideoImportModel.urlAlreadyImported({ channelId: channel.id, channelSyncId: channelSync?.id, targetUrl })) {
     logger.debug(
@@ -110,7 +110,7 @@ async function skipImport (options: {
     return true
   }
 
-  if (onlyAfter) {
+  if (skipPublishedBefore) {
     const youtubeDL = new YoutubeDLWrapper(
       targetUrl,
       ServerConfigManager.Instance.getEnabledResolutions('vod'),
@@ -119,7 +119,7 @@ async function skipImport (options: {
 
     const videoInfo = await youtubeDL.getInfoForDownload()
 
-    const onlyAfterWithoutTime = new Date(onlyAfter)
+    const onlyAfterWithoutTime = new Date(skipPublishedBefore)
     onlyAfterWithoutTime.setHours(0, 0, 0, 0)
 
     if (videoInfo.originallyPublishedAtWithoutTime.getTime() < onlyAfterWithoutTime.getTime()) {