diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java b/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java
index 380455c2ca6a..a6884db857a2 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/EditPostActivity.java
@@ -3347,7 +3347,7 @@ public boolean onMediaRetryClicked(final String mediaId) {
             mEditorMedia.retryFailedMediaAsync(Collections.singletonList(media.getId()));
         }
 
-        AnalyticsTracker.track(Stat.EDITOR_UPLOAD_MEDIA_RETRIED);
+        AnalyticsUtils.trackWithSiteDetails(Stat.EDITOR_UPLOAD_MEDIA_RETRIED, mSite);
         return true;
     }
 
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/EditorMedia.kt b/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/EditorMedia.kt
index e31635fa54ec..0edca25c46ee 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/EditorMedia.kt
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/EditorMedia.kt
@@ -39,6 +39,7 @@ import org.wordpress.android.util.NetworkUtilsWrapper
 import org.wordpress.android.util.StringUtils
 import org.wordpress.android.util.ToastUtils.Duration
 import org.wordpress.android.util.analytics.AnalyticsTrackerWrapper
+import org.wordpress.android.util.analytics.AnalyticsUtils
 import org.wordpress.android.util.analytics.AnalyticsUtilsWrapper
 import org.wordpress.android.viewmodel.Event
 import org.wordpress.android.viewmodel.SingleLiveEvent
@@ -295,7 +296,11 @@ class EditorMedia @Inject constructor(
                     it["error_type"] = error.type.name
                 }
         }
-        analyticsTrackerWrapper.track(EDITOR_UPLOAD_MEDIA_FAILED, properties)
+        AnalyticsUtils.trackWithSiteDetails(
+            analyticsTrackerWrapper,
+            EDITOR_UPLOAD_MEDIA_FAILED,
+            site,
+            properties)
         listener.onMediaUploadFailed(media.id.toString())
     }
 
diff --git a/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCase.kt b/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCase.kt
index 1a00989a78ce..8ae1a20c0480 100644
--- a/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCase.kt
+++ b/WordPress/src/main/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCase.kt
@@ -3,7 +3,10 @@ package org.wordpress.android.ui.posts.editor.media
 import dagger.Reusable
 import org.wordpress.android.analytics.AnalyticsTracker.Stat
 import org.wordpress.android.fluxc.model.MediaModel.MediaUploadState.QUEUED
+import org.wordpress.android.fluxc.model.SiteModel
+import org.wordpress.android.fluxc.store.SiteStore
 import org.wordpress.android.util.analytics.AnalyticsTrackerWrapper
+import org.wordpress.android.util.analytics.AnalyticsUtils
 import javax.inject.Inject
 
 @Reusable
@@ -11,7 +14,8 @@ class RetryFailedMediaUploadUseCase @Inject constructor(
     private val getMediaModelUseCase: GetMediaModelUseCase,
     private val updateMediaModelUseCase: UpdateMediaModelUseCase,
     private val uploadMediaUseCase: UploadMediaUseCase,
-    private val tracker: AnalyticsTrackerWrapper
+    private val tracker: AnalyticsTrackerWrapper,
+    private val siteStore: SiteStore
 ) {
     suspend fun retryFailedMediaAsync(
         editorMediaListener: EditorMediaListener,
@@ -33,7 +37,9 @@ class RetryFailedMediaUploadUseCase @Inject constructor(
                         editorMediaListener,
                         mediaModels
                     )
-                    tracker.track(Stat.EDITOR_UPLOAD_MEDIA_RETRIED)
+                    val siteId = editorMediaListener.getImmutablePost().localSiteId
+                    val site: SiteModel? = siteStore.getSiteByLocalId(siteId)
+                    AnalyticsUtils.trackWithSiteDetails(tracker, Stat.EDITOR_UPLOAD_MEDIA_RETRIED, site, null);
                 }
             }
     }
diff --git a/WordPress/src/test/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCaseTest.kt b/WordPress/src/test/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCaseTest.kt
index 366303e9fe00..c51bbaa40fbb 100644
--- a/WordPress/src/test/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCaseTest.kt
+++ b/WordPress/src/test/java/org/wordpress/android/ui/posts/editor/media/RetryFailedMediaUploadUseCaseTest.kt
@@ -18,6 +18,8 @@ import org.wordpress.android.analytics.AnalyticsTracker.Stat
 import org.wordpress.android.fluxc.model.MediaModel
 import org.wordpress.android.fluxc.model.MediaModel.MediaUploadState
 import org.wordpress.android.fluxc.model.MediaModel.MediaUploadState.QUEUED
+import org.wordpress.android.fluxc.model.PostImmutableModel
+import org.wordpress.android.fluxc.store.SiteStore
 import org.wordpress.android.util.analytics.AnalyticsTrackerWrapper
 
 @ExperimentalCoroutinesApi
@@ -29,8 +31,9 @@ class RetryFailedMediaUploadUseCaseTest : BaseUnitTest() {
         val getMediaModelUseCase = createGetMediaModelUseCase()
         val useCase = createUseCase(getMediaModelUseCase = getMediaModelUseCase)
 
+
         // Act
-        useCase.retryFailedMediaAsync(mock(), FAILED_MEDIA_IDS)
+        useCase.retryFailedMediaAsync(createEditorMediaListener(), FAILED_MEDIA_IDS)
         // Assert
         verify(getMediaModelUseCase).loadMediaByLocalId(FAILED_MEDIA_IDS)
     }
@@ -42,7 +45,7 @@ class RetryFailedMediaUploadUseCaseTest : BaseUnitTest() {
         val useCase = createUseCase(updateMediaModelUseCase = updateMediaModelUseCase)
 
         // Act
-        useCase.retryFailedMediaAsync(mock(), FAILED_MEDIA_IDS)
+        useCase.retryFailedMediaAsync(createEditorMediaListener(), FAILED_MEDIA_IDS)
 
         // Assert
         verify(updateMediaModelUseCase, times(FAILED_MEDIA_IDS.size)).updateMediaModel(
@@ -59,7 +62,7 @@ class RetryFailedMediaUploadUseCaseTest : BaseUnitTest() {
         val useCase = createUseCase(uploadMediaUseCase = uploadMediaUseCase)
 
         // Act
-        useCase.retryFailedMediaAsync(mock(), FAILED_MEDIA_IDS)
+        useCase.retryFailedMediaAsync(createEditorMediaListener(), FAILED_MEDIA_IDS)
 
         // Assert
         verify(uploadMediaUseCase).saveQueuedPostAndStartUpload(
@@ -74,7 +77,7 @@ class RetryFailedMediaUploadUseCaseTest : BaseUnitTest() {
         val trackerWrapper: AnalyticsTrackerWrapper = mock()
         val useCase = createUseCase(tracker = trackerWrapper)
         // Act
-        useCase.retryFailedMediaAsync(mock(), FAILED_MEDIA_IDS)
+        useCase.retryFailedMediaAsync(createEditorMediaListener(), FAILED_MEDIA_IDS)
         // Assert
         verify(trackerWrapper).track(Stat.EDITOR_UPLOAD_MEDIA_RETRIED)
     }
@@ -112,13 +115,15 @@ class RetryFailedMediaUploadUseCaseTest : BaseUnitTest() {
             getMediaModelUseCase: GetMediaModelUseCase = createGetMediaModelUseCase(),
             updateMediaModelUseCase: UpdateMediaModelUseCase = mock(),
             uploadMediaUseCase: UploadMediaUseCase = mock(),
-            tracker: AnalyticsTrackerWrapper = mock()
+            tracker: AnalyticsTrackerWrapper = mock(),
+            siteStore: SiteStore = mock()
         ): RetryFailedMediaUploadUseCase {
             return RetryFailedMediaUploadUseCase(
                 getMediaModelUseCase,
                 updateMediaModelUseCase,
                 uploadMediaUseCase,
-                tracker
+                tracker,
+                siteStore
             )
         }
 
@@ -136,5 +141,13 @@ class RetryFailedMediaUploadUseCaseTest : BaseUnitTest() {
                 this.id = mediaModelId
                 this.uploadState = MediaUploadState.FAILED.name
             }
+
+        fun createEditorMediaListener() = mock<EditorMediaListener> {
+            on { getImmutablePost() } doAnswer {
+                mock<PostImmutableModel> {
+                    on { localSiteId } doAnswer { 0 }
+                }
+            }
+        }
     }
 }