diff --git a/src/Logic/ImageProviders/ImageUploadManager.ts b/src/Logic/ImageProviders/ImageUploadManager.ts
index a39f88c061..7a0e3b1607 100644
--- a/src/Logic/ImageProviders/ImageUploadManager.ts
+++ b/src/Logic/ImageProviders/ImageUploadManager.ts
@@ -3,7 +3,7 @@ import LinkImageAction from "../Osm/Actions/LinkImageAction"
 import FeaturePropertiesStore from "../FeatureSource/Actors/FeaturePropertiesStore"
 import { NoteId, OsmId, OsmTags } from "../../Models/OsmFeature"
 import ThemeConfig from "../../Models/ThemeConfig/ThemeConfig"
-import { Store, UIEventSource } from "../UIEventSource"
+import { Store, Stores, UIEventSource } from "../UIEventSource"
 import { OsmConnection } from "../Osm/OsmConnection"
 import { Changes } from "../Osm/Changes"
 import Translations from "../../UI/i18n/Translations"
@@ -80,6 +80,10 @@ export class ImageUploadManager {
         this._changes = changes
         this._gps = gpsLocation
         this._reportError = reportError
+        Stores.Chronic(5 * 60000).addCallback(() => {
+            // If images failed to upload: attempt to reupload
+            this.uploadQueue()
+        })
     }
 
     public async canBeUploaded(file: File): Promise<true | { error: Translation }> {
@@ -166,16 +170,26 @@ export class ImageUploadManager {
         if (this.uploadingAll) {
             return
         }
-        const queue = this._queue.imagesInQueue.data ?? []
+        let queue = this._queue.imagesInQueue.data ?? []
         if (queue.length === 0) {
             return
         }
         console.log("Checking image upload queue and uploading if needed")
         this.uploadingAll = true
         try {
+            queue = [...queue]
             while (queue.length > 0) {
-                const currentItem = queue[0]
-                await this.handleQueueItem(currentItem)
+                const currentItem = queue.shift()
+                if(!currentItem){
+                    continue
+                }
+                const uploadOk = await this.handleQueueItem(currentItem)
+                if(uploadOk){
+                    this._queue.delete(currentItem)
+                }else{
+                    // Our local 'queue' is a copy where we've removed the failed item from
+                    // A next attempt to 'uploadQueue' will retry the upload
+                }
             }
         } catch (e) {
             console.error("Error while handling the queue:", e)
@@ -192,14 +206,11 @@ export class ImageUploadManager {
      * - Applies the action to the correct element
      * - indicates failure
      *
-     * Modifies the queue: if the upload is successfull, deletes the item from the queue
-     * @private
+     * Will _not_ modify the queue: if the upload is successful, deletes the item from the queue.
+     * @returns true if successful (and the item should be deleted from the queue), false if something failed
      */
-    private async handleQueueItem(args: ImageUploadArguments): Promise<void> {
+    private async handleQueueItem(args: NonNullable<ImageUploadArguments>): Promise<boolean> {
         console.log("Handling queue item", args.blob.name, args)
-        if (!args) {
-            return
-        }
         this._isUploading.set(args.featureId)
 
         let result: UploadResult = undefined
@@ -221,7 +232,7 @@ export class ImageUploadManager {
         if (result === undefined) {
             this._fails.data.push(args)
             this._fails.ping()
-            return
+            return false
         }
         let properties: UIEventSource<Record<string, string>> = this._featureProperties.getStore(
             args.featureId
@@ -239,34 +250,33 @@ export class ImageUploadManager {
                     osmConnection: this._osmConnection,
                 })
             }
-        } else {
-            if (properties === undefined) {
-                const downloaded = await new OsmObjectDownloader(
-                    this._osmConnection.Backend(),
-                    this._changes
-                ).DownloadObjectAsync(args.featureId)
-                if (downloaded === "deleted") {
-                    this._queue.delete(args)
-                    return
-                }
-                this._featureProperties.trackFeature(downloaded.asGeoJson())
-                properties = this._featureProperties.getStore(args.featureId)
-            }
-            const action = new LinkImageAction(
-                args.featureId,
-                result.key,
-                result.value,
-                properties,
-                {
-                    theme: args.layoutId ?? properties?.data?.["_orig_theme"] ?? this._theme.id,
-                    changeType: "add-image",
-                }
-            )
-            await this._changes.applyAction(action)
-            await this._changes.flushChanges("Image upload completed")
+            return true
         }
-
-        this._queue.delete(args)
+        if (properties === undefined) {
+            const downloaded = await new OsmObjectDownloader(
+                this._osmConnection.Backend(),
+                this._changes,
+            ).DownloadObjectAsync(args.featureId)
+            if (downloaded === "deleted") {
+                this._queue.delete(args)
+                return
+            }
+            this._featureProperties.trackFeature(downloaded.asGeoJson())
+            properties = this._featureProperties.getStore(args.featureId)
+        }
+        const action = new LinkImageAction(
+            args.featureId,
+            result.key,
+            result.value,
+            properties,
+            {
+                theme: args.layoutId ?? properties?.data?.["_orig_theme"] ?? this._theme.id,
+                changeType: "add-image",
+            },
+        )
+        await this._changes.applyAction(action)
+        await this._changes.flushChanges("Image upload completed")
+        return true
     }
 
     /**