diff --git a/resources/i18n/en.json5 b/resources/i18n/en.json5
index b9c01f3ab4..bc6f4991fd 100644
--- a/resources/i18n/en.json5
+++ b/resources/i18n/en.json5
@@ -270,12 +270,14 @@
   "home.top-level-communities.head": "Communities in DSpace",
   "home.top-level-communities.help": "Select a community to browse its collections.",
 
-  "item.bitstreams.upload.bundle-name": "Bundle Name",
+  "item.bitstreams.upload.bundle": "Bundle",
+  "item.bitstreams.upload.bundles.empty": "This item doesn\'t contain any bundles to upload a bitstream to.",
   "item.bitstreams.upload.drop-message": "Drop a file to upload",
   "item.bitstreams.upload.failed": "Upload failed. Please verify the content before retrying.",
   "item.bitstreams.upload.item": "Item: ",
   "item.bitstreams.upload.title": "Upload bitstream",
 
+  "item.edit.bitstreams.bundle.edit.buttons.upload": "Upload",
   "item.edit.bitstreams.bundle.name": "BUNDLE: {{ name }}",
   "item.edit.bitstreams.discard-button": "Discard",
   "item.edit.bitstreams.edit.buttons.download": "Download",
diff --git a/src/app/+item-page/bitstreams/upload/upload-bitstream.component.html b/src/app/+item-page/bitstreams/upload/upload-bitstream.component.html
index 75d31ee34e..9556dbe705 100644
--- a/src/app/+item-page/bitstreams/upload/upload-bitstream.component.html
+++ b/src/app/+item-page/bitstreams/upload/upload-bitstream.component.html
@@ -1,28 +1,36 @@
-<div class="container">
-  <div class="row">
-    <div class="col-12 mb-4">
-      <h2>{{'item.bitstreams.upload.title' | translate}}</h2>
-      <ng-container *ngVar="(itemRD$ | async)?.payload as item">
-        <div *ngIf="item">
-          <span class="font-weight-bold">{{'item.bitstreams.upload.item' | translate}}</span>
-          <span>{{item.name}}</span>
+<div class="container" *ngVar="(bundlesRD$ | async)?.payload?.page as bundles">
+  <ng-container *ngIf="bundles">
+    <div class="row" *ngIf="bundles.length > 0">
+      <div class="col-12 mb-4">
+        <h2>{{'item.bitstreams.upload.title' | translate}}</h2>
+        <ng-container *ngVar="(itemRD$ | async)?.payload as item">
+          <div *ngIf="item">
+            <span class="font-weight-bold">{{'item.bitstreams.upload.item' | translate}}</span>
+            <span>{{item.name}}</span>
+          </div>
+        </ng-container>
+      </div>
+      <div class="col-12">
+        <label for="bundleName" class="font-weight-bold">{{'item.bitstreams.upload.bundle' | translate}}</label>
+        <select id="bundleName" class="form-control" [(ngModel)]="selectedBundleId" (change)="setUploadUrl()">
+          <option *ngFor="let bundle of bundles" [value]="bundle.id">{{bundle.name}}</option>
+        </select>
+        <ds-uploader  class="w-100"
+                      [dropMsg]="'item.bitstreams.upload.drop-message'"
+                      [dropOverDocumentMsg]="'item.bitstreams.upload.drop-message'"
+                      [enableDragOverDocument]="true"
+                      [uploadFilesOptions]="uploadFilesOptions"
+                      [uploadProperties]="uploadProperties"
+                      (onCompleteItem)="onCompleteItem($event)"
+                      (onUploadError)="onUploadError()"></ds-uploader>
+      </div>
+    </div>
+    <div class="row" *ngIf="bundles.length === 0">
+      <div class="col-12">
+        <div class="alert alert-info w-100 d-inline-block" role="alert">
+          {{'item.bitstreams.upload.bundles.empty' | translate}}
         </div>
-      </ng-container>
+      </div>
     </div>
-    <div class="col-12">
-      <label for="bundleName" class="font-weight-bold">{{'item.bitstreams.upload.bundle-name' | translate}}</label>
-      <input  id="bundleName"
-              [(ngModel)]="uploadProperties.bundleName"
-              type="text"
-              class="form-control" />
-      <ds-uploader  class="w-100"
-                    [dropMsg]="'item.bitstreams.upload.drop-message'"
-                    [dropOverDocumentMsg]="'item.bitstreams.upload.drop-message'"
-                    [enableDragOverDocument]="true"
-                    [uploadFilesOptions]="uploadFilesOptions"
-                    [uploadProperties]="uploadProperties"
-                    (onCompleteItem)="onCompleteItem($event)"
-                    (onUploadError)="onUploadError()"></ds-uploader>
-    </div>
-  </div>
+  </ng-container>
 </div>
diff --git a/src/app/+item-page/bitstreams/upload/upload-bitstream.component.ts b/src/app/+item-page/bitstreams/upload/upload-bitstream.component.ts
index 3caf8b586d..13ac76591a 100644
--- a/src/app/+item-page/bitstreams/upload/upload-bitstream.component.ts
+++ b/src/app/+item-page/bitstreams/upload/upload-bitstream.component.ts
@@ -2,17 +2,20 @@ import { ChangeDetectionStrategy, Component, OnDestroy, OnInit } from '@angular/
 import { Observable } from 'rxjs/internal/Observable';
 import { RemoteData } from '../../../core/data/remote-data';
 import { Item } from '../../../core/shared/item.model';
-import { distinctUntilChanged, map, switchMap } from 'rxjs/operators';
+import { map, switchMap, take } from 'rxjs/operators';
 import { ActivatedRoute, Router } from '@angular/router';
 import { UploaderOptions } from '../../../shared/uploader/uploader-options.model';
 import { Subscription } from 'rxjs/internal/Subscription';
-import { hasValue, hasValueOperator } from '../../../shared/empty.util';
+import { hasValue, isEmpty } from '../../../shared/empty.util';
 import { ItemDataService } from '../../../core/data/item-data.service';
 import { AuthService } from '../../../core/auth/auth.service';
 import { NotificationsService } from '../../../shared/notifications/notifications.service';
 import { TranslateService } from '@ngx-translate/core';
-import { UploaderProperties } from '../../../shared/uploader/uploader-properties.model';
 import { getBitstreamModulePath } from '../../../app-routing.module';
+import { PaginatedList } from '../../../core/data/paginated-list';
+import { Bundle } from '../../../core/shared/bundle.model';
+import { BundleDataService } from '../../../core/data/bundle-data.service';
+import { getRemoteDataPayload, getSucceededRemoteData } from '../../../core/shared/operators';
 
 @Component({
   selector: 'ds-upload-bitstream',
@@ -29,12 +32,23 @@ export class UploadBitstreamComponent implements OnInit, OnDestroy {
    */
   itemRD$: Observable<RemoteData<Item>>;
 
+  /**
+   * The item's bundles
+   */
+  bundlesRD$: Observable<RemoteData<PaginatedList<Bundle>>>;
+
+  /**
+   * The ID of the currently selected bundle to upload a bitstream to
+   */
+  selectedBundleId: string;
+
   /**
    * The uploader configuration options
    * @type {UploaderOptions}
    */
   uploadFilesOptions: UploaderOptions = {
-    url: '',
+    // URL needs to contain something to not produce any errors. This will be replaced once a bundle has been selected.
+    url: 'placeholder',
     authToken: null,
     disableMultipart: false,
     itemAlias: null
@@ -46,16 +60,10 @@ export class UploadBitstreamComponent implements OnInit, OnDestroy {
    */
   subs: Subscription[] = [];
 
-  /**
-   * Properties to send with the upload request
-   */
-  uploadProperties = Object.assign(new UploaderProperties(), {
-    bundleName: 'ORIGINAL'
-  });
-
   constructor(protected route: ActivatedRoute,
               protected router: Router,
               protected itemService: ItemDataService,
+              protected bundleService: BundleDataService,
               protected authService: AuthService,
               protected notificationsService: NotificationsService,
               protected translate: TranslateService) {
@@ -63,25 +71,36 @@ export class UploadBitstreamComponent implements OnInit, OnDestroy {
 
   ngOnInit(): void {
     this.itemRD$ = this.route.data.pipe(map((data) => data.item));
-    this.subs.push(
-      this.route.queryParams.pipe(
-        map((params) => params.bundleName),
-        hasValueOperator(),
-        distinctUntilChanged()
-      ).subscribe((bundleName: string) => {
-        this.uploadProperties.bundleName = bundleName;
-      })
+    this.bundlesRD$ = this.itemRD$.pipe(
+      switchMap((itemRD: RemoteData<Item>) => itemRD.payload.bundles)
     );
-    this.subs.push(
-      this.itemRD$.pipe(
-        map((itemRD: RemoteData<Item>) => itemRD.payload),
-        switchMap((item: Item) => this.itemService.getBitstreamsEndpoint(item.id)),
-        distinctUntilChanged()
-      ).subscribe((url: string) => {
-        this.uploadFilesOptions.url = url;
+    this.selectedBundleId = this.route.snapshot.queryParams.bundle;
+    if (isEmpty(this.selectedBundleId)) {
+      this.bundlesRD$.pipe(
+        getSucceededRemoteData(),
+        getRemoteDataPayload(),
+        take(1)
+      ).subscribe((bundles: PaginatedList<Bundle>) => {
+        if (bundles.page.length > 0) {
+          this.selectedBundleId = bundles.page[0].id;
+          this.setUploadUrl();
+        }
+      });
+    } else {
+      this.setUploadUrl();
+    }
+  }
+
+  /**
+   * Set the upload url to match the selected bundle ID
+   */
+  setUploadUrl() {
+    this.bundleService.getBitstreamsEndpoint(this.selectedBundleId).pipe(take(1)).subscribe((href: string) => {
+      this.uploadFilesOptions.url = href;
+      if (isEmpty(this.uploadFilesOptions.authToken)) {
         this.uploadFilesOptions.authToken = this.authService.buildAuthHeader();
-      })
-    );
+      }
+    });
   }
 
   /**
diff --git a/src/app/+item-page/edit-item-page/edit-item-page.module.ts b/src/app/+item-page/edit-item-page/edit-item-page.module.ts
index 4f73cbeaf1..2b48141011 100644
--- a/src/app/+item-page/edit-item-page/edit-item-page.module.ts
+++ b/src/app/+item-page/edit-item-page/edit-item-page.module.ts
@@ -24,6 +24,7 @@ import { EditRelationshipListComponent } from './item-relationships/edit-relatio
 import { AbstractItemUpdateComponent } from './abstract-item-update/abstract-item-update.component';
 import { ItemMoveComponent } from './item-move/item-move.component';
 import { ItemEditBitstreamBundleComponent } from './item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component';
+import { BundleDataService } from '../../core/data/bundle-data.service';
 
 /**
  * Module that contains all components related to the Edit Item page administrator functionality
@@ -58,6 +59,9 @@ import { ItemEditBitstreamBundleComponent } from './item-bitstreams/item-edit-bi
     EditRelationshipListComponent,
     ItemCollectionMapperComponent,
     ItemMoveComponent,
+  ],
+  providers: [
+    BundleDataService
   ]
 })
 export class EditItemPageModule {
diff --git a/src/app/+item-page/edit-item-page/item-bitstreams/item-bitstreams.component.html b/src/app/+item-page/edit-item-page/item-bitstreams/item-bitstreams.component.html
index ddcff0c207..dc0acda61a 100644
--- a/src/app/+item-page/edit-item-page/item-bitstreams/item-bitstreams.component.html
+++ b/src/app/+item-page/edit-item-page/item-bitstreams/item-bitstreams.component.html
@@ -23,7 +23,7 @@
     </button>
   </div>
 
-  <table *ngIf="bundles?.length > 0" class="table table-responsive table-striped table-bordered mt-4">
+  <table *ngIf="item && bundles?.length > 0" class="table table-responsive table-striped table-bordered mt-4">
     <tbody>
       <tr>
         <th>{{'item.edit.bitstreams.headers.name' | translate}}</th>
@@ -33,7 +33,8 @@
       </tr>
       <ds-item-edit-bitstream-bundle *ngFor="let bundle of bundles"
                                      [url]="url"
-                                     [bundle]="bundle">
+                                     [bundle]="bundle"
+                                     [item]="item">
       </ds-item-edit-bitstream-bundle>
     </tbody>
   </table>
diff --git a/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.html b/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.html
index 4be9ee2610..5baa4e04b4 100644
--- a/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.html
+++ b/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.html
@@ -1,6 +1,16 @@
 <ng-template #bundleView>
   <tr>
-    <td colspan="4">{{'item.edit.bitstreams.bundle.name' | translate:{ name: bundle.name } }}</td>
+    <td colspan="3" class="font-weight-bold">{{'item.edit.bitstreams.bundle.name' | translate:{ name: bundle.name } }}</td>
+    <td class="text-center">
+      <div class="btn-group bundle-action-buttons">
+        <button [routerLink]="['/items/', item.id, 'bitstreams', 'new']"
+                [queryParams]="{bundle: bundle.id}"
+                class="btn btn-outline-success btn-sm"
+                title="{{'item.edit.bitstreams.bundle.edit.buttons.upload' | translate}}">
+          <i class="fas fa-upload fa-fw"></i>
+        </button>
+      </div>
+    </td>
   </tr>
   <ng-container *ngVar="((updates$ | async) | dsObjectValues) as updateValues">
     <tr *ngFor="let updateValue of updateValues"
diff --git a/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.ts b/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.ts
index 87774a3f17..be1ae542fb 100644
--- a/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.ts
+++ b/src/app/+item-page/edit-item-page/item-bitstreams/item-edit-bitstream-bundle/item-edit-bitstream-bundle.component.ts
@@ -6,6 +6,7 @@ import { FieldUpdates } from '../../../../core/data/object-updates/object-update
 import { toBitstreamsArray } from '../../../../core/shared/item-bitstreams-utils';
 import { switchMap } from 'rxjs/operators';
 import { Bitstream } from '../../../../core/shared/bitstream.model';
+import { Item } from '../../../../core/shared/item.model';
 
 @Component({
   selector: 'ds-item-edit-bitstream-bundle',
@@ -26,6 +27,11 @@ export class ItemEditBitstreamBundleComponent implements OnInit {
    */
   @Input() bundle: Bundle;
 
+  /**
+   * The item the bundle belongs to
+   */
+  @Input() item: Item;
+
   /**
    * The current url of this page
    */
diff --git a/src/app/core/data/bundle-data.service.ts b/src/app/core/data/bundle-data.service.ts
index 5962488c4f..c3857b5877 100644
--- a/src/app/core/data/bundle-data.service.ts
+++ b/src/app/core/data/bundle-data.service.ts
@@ -13,6 +13,7 @@ import { HttpClient } from '@angular/common/http';
 import { DefaultChangeAnalyzer } from './default-change-analyzer.service';
 import { FindAllOptions } from './request.models';
 import { Observable } from 'rxjs/internal/Observable';
+import { switchMap } from 'rxjs/operators';
 
 /**
  * A service responsible for fetching/sending data from/to the REST API on the bundles endpoint
@@ -20,6 +21,7 @@ import { Observable } from 'rxjs/internal/Observable';
 @Injectable()
 export class BundleDataService extends DataService<Bundle> {
   protected linkPath = 'bundles';
+  protected bitstreamsEndpoint = 'bitstreams';
   protected forceBypassCache = false;
 
   constructor(
@@ -43,4 +45,14 @@ export class BundleDataService extends DataService<Bundle> {
   getBrowseEndpoint(options: FindAllOptions = {}, linkPath?: string): Observable<string> {
     return this.halService.getEndpoint(this.linkPath);
   }
+
+  /**
+   * Get the bitstreams endpoint for a bundle
+   * @param bundleId
+   */
+  getBitstreamsEndpoint(bundleId: string): Observable<string> {
+    return this.getBrowseEndpoint().pipe(
+      switchMap((href: string) => this.halService.getEndpoint(this.bitstreamsEndpoint, `${href}/${bundleId}`))
+    );
+  }
 }