diff --git a/packages/next/src/views/List/Default/index.tsx b/packages/next/src/views/List/Default/index.tsx
index c29e2eccd..2e7c37353 100644
--- a/packages/next/src/views/List/Default/index.tsx
+++ b/packages/next/src/views/List/Default/index.tsx
@@ -133,19 +133,31 @@ export const DefaultListView: React.FC = () => {
           {Header || (
             <ListHeader heading={getTranslation(labels?.plural, i18n)}>
               {hasCreatePermission && (
-                <Button
-                  Link={!isBulkUploadEnabled ? Link : undefined}
-                  aria-label={i18n.t('general:createNewLabel', {
-                    label: getTranslation(labels?.singular, i18n),
-                  })}
-                  buttonStyle="pill"
-                  el={!isBulkUploadEnabled ? 'link' : 'button'}
-                  onClick={isBulkUploadEnabled ? openBulkUpload : undefined}
-                  size="small"
-                  to={!isBulkUploadEnabled ? newDocumentURL : undefined}
-                >
-                  {i18n.t('general:createNew')}
-                </Button>
+                <>
+                  <Button
+                    Link={Link}
+                    aria-label={i18n.t('general:createNewLabel', {
+                      label: getTranslation(labels?.singular, i18n),
+                    })}
+                    buttonStyle="pill"
+                    el={'link'}
+                    size="small"
+                    to={newDocumentURL}
+                  >
+                    {i18n.t('general:createNew')}
+                  </Button>
+
+                  {isBulkUploadEnabled && (
+                    <Button
+                      aria-label={t('upload:bulkUpload')}
+                      buttonStyle="pill"
+                      onClick={openBulkUpload}
+                      size="small"
+                    >
+                      {t('upload:bulkUpload')}
+                    </Button>
+                  )}
+                </>
               )}
               {!smallBreak && (
                 <ListSelection label={getTranslation(collectionConfig.labels.plural, i18n)} />
diff --git a/packages/ui/src/elements/BulkUpload/AddFilesView/index.tsx b/packages/ui/src/elements/BulkUpload/AddFilesView/index.tsx
index 4ebc8fb6e..18e0b5269 100644
--- a/packages/ui/src/elements/BulkUpload/AddFilesView/index.tsx
+++ b/packages/ui/src/elements/BulkUpload/AddFilesView/index.tsx
@@ -40,6 +40,7 @@ export function AddFilesView({ onCancel, onDrop }: Props) {
             aria-hidden="true"
             className={`${baseClass}__hidden-input`}
             hidden
+            multiple
             onChange={(e) => {
               if (e.target.files && e.target.files.length > 0) {
                 onDrop(e.target.files)
@@ -53,7 +54,6 @@ export function AddFilesView({ onCancel, onDrop }: Props) {
             {t('general:or')} {t('upload:dragAndDrop')}
           </p>
         </Dropzone>
-        {/* <Dropzone multipleFiles onChange={onDrop} /> */}
       </div>
     </div>
   )
diff --git a/packages/ui/src/elements/Dropzone/index.scss b/packages/ui/src/elements/Dropzone/index.scss
index 3e336c64f..c1dbb1d94 100644
--- a/packages/ui/src/elements/Dropzone/index.scss
+++ b/packages/ui/src/elements/Dropzone/index.scss
@@ -4,7 +4,7 @@
   position: relative;
   display: flex;
   align-items: center;
-  padding: calc(var(--base) * .9) calc(var(--base) / 2);
+  padding: calc(var(--base) * .9) var(--base);
   background: transparent;
   border: 1px dotted var(--theme-elevation-400);
   border-radius: var(--style-radius-s);
diff --git a/packages/ui/src/elements/Table/DefaultCell/fields/File/index.scss b/packages/ui/src/elements/Table/DefaultCell/fields/File/index.scss
index 14ea81fac..846db8b63 100644
--- a/packages/ui/src/elements/Table/DefaultCell/fields/File/index.scss
+++ b/packages/ui/src/elements/Table/DefaultCell/fields/File/index.scss
@@ -3,21 +3,21 @@
 .file {
   display: flex;
   flex-wrap: nowrap;
-  margin: base(-0.25) 0;
 
   &__thumbnail {
     display: inline-block;
-    max-width: base(3);
-    height: base(3);
+    max-width: calc(var(--base) * 2);
+    height: calc(var(--base) * 2);
+    border-radius: var(--style-radius-s);
   }
 
   &__filename {
     align-self: center;
     [dir='ltr'] & {
-      margin-left: base(1);
+      margin-left: var(--base);
     }
     [dir='rtl'] & {
-      margin-right: base(1);
+      margin-right: var(--base);
     }
   }
 }
diff --git a/packages/ui/src/elements/Upload/index.scss b/packages/ui/src/elements/Upload/index.scss
index e26eb86b3..4f687eeb1 100644
--- a/packages/ui/src/elements/Upload/index.scss
+++ b/packages/ui/src/elements/Upload/index.scss
@@ -28,6 +28,7 @@
       width: 100%;
       height: 100%;
       object-fit: contain;
+      border-radius: var(--style-radius-s) 0 0 var(--style-radius-s);
     }
   }
 
@@ -85,11 +86,30 @@
 
   .dropzone {
     background-color: transparent;
+    padding-block: calc(var(--base) * 2.25);
+  }
+
+  &__dropzoneContent {
+    display: flex;
+    justify-content: space-between;
+    width: 100%;
   }
 
   &__dropzoneButtons {
     display: flex;
-    gap: var(--base);
+    gap: calc(var(--base) * .5);
+  }
+
+  &__orText {
+    color: var(--theme-elevation-500);
+    text-transform: lowercase;
+  }
+
+  &__dragAndDropText {
+    margin: 0;
+    text-transform: lowercase;
+    align-self: center;
+    color: var(--theme-elevation-500);
   }
 
   @include small-break {
@@ -123,4 +143,10 @@
       display: none;
     }
   }
+
+  @include small-break {
+    &__dropzoneContent {
+      display: none;
+    }
+  }
 }
diff --git a/packages/ui/src/elements/Upload/index.tsx b/packages/ui/src/elements/Upload/index.tsx
index b50a6df65..995e860c0 100644
--- a/packages/ui/src/elements/Upload/index.tsx
+++ b/packages/ui/src/elements/Upload/index.tsx
@@ -235,43 +235,46 @@ export const Upload: React.FC<UploadProps> = (props) => {
         <div className={`${baseClass}__upload`}>
           {!value && !showUrlInput && (
             <Dropzone onChange={handleFileSelection}>
-              <div className={`${baseClass}__dropzoneButtons`}>
-                <Button
-                  buttonStyle="icon-label"
-                  icon="plus"
-                  iconPosition="left"
-                  onClick={() => {
-                    if (inputRef.current) {
-                      inputRef.current.click()
-                    }
-                  }}
-                  size="small"
-                >
-                  {t('upload:selectFile')}
-                </Button>
-                <input
-                  aria-hidden="true"
-                  className={`${baseClass}__hidden-input`}
-                  hidden
-                  onChange={(e) => {
-                    if (e.target.files && e.target.files.length > 0) {
-                      handleFileSelection(e.target.files)
-                    }
-                  }}
-                  ref={inputRef}
-                  type="file"
-                />
-                <Button
-                  buttonStyle="icon-label"
-                  icon="link"
-                  iconPosition="left"
-                  onClick={() => {
-                    setShowUrlInput(true)
-                  }}
-                  size="small"
-                >
-                  {t('upload:pasteURL')}
-                </Button>
+              <div className={`${baseClass}__dropzoneContent`}>
+                <div className={`${baseClass}__dropzoneButtons`}>
+                  <Button
+                    buttonStyle="pill"
+                    onClick={() => {
+                      if (inputRef.current) {
+                        inputRef.current.click()
+                      }
+                    }}
+                    size="small"
+                  >
+                    {t('upload:selectFile')}
+                  </Button>
+                  <input
+                    aria-hidden="true"
+                    className={`${baseClass}__hidden-input`}
+                    hidden
+                    onChange={(e) => {
+                      if (e.target.files && e.target.files.length > 0) {
+                        handleFileSelection(e.target.files)
+                      }
+                    }}
+                    ref={inputRef}
+                    type="file"
+                  />
+                  <span className={`${baseClass}__orText`}>{t('general:or')}</span>
+                  <Button
+                    buttonStyle="pill"
+                    onClick={() => {
+                      setShowUrlInput(true)
+                    }}
+                    size="small"
+                  >
+                    {t('upload:pasteURL')}
+                  </Button>
+                </div>
+
+                <p className={`${baseClass}__dragAndDropText`}>
+                  {t('general:or')} {t('upload:dragAndDrop')}
+                </p>
               </div>
             </Dropzone>
           )}
diff --git a/packages/ui/src/fields/Upload/Input.tsx b/packages/ui/src/fields/Upload/Input.tsx
index 1ad5dce38..1609b4a93 100644
--- a/packages/ui/src/fields/Upload/Input.tsx
+++ b/packages/ui/src/fields/Upload/Input.tsx
@@ -25,9 +25,11 @@ import type { ListDrawerProps } from '../../elements/ListDrawer/types.js'
 
 import { useBulkUpload } from '../../elements/BulkUpload/index.js'
 import { Button } from '../../elements/Button/index.js'
+import { useDocumentDrawer } from '../../elements/DocumentDrawer/index.js'
 import { Dropzone } from '../../elements/Dropzone/index.js'
 import { useListDrawer } from '../../elements/ListDrawer/index.js'
 import { ShimmerEffect } from '../../elements/ShimmerEffect/index.js'
+import { PlusIcon } from '../../icons/Plus/index.js'
 import { useAuth } from '../../providers/Auth/index.js'
 import { useLocale } from '../../providers/Locale/index.js'
 import { useTranslation } from '../../providers/Translation/index.js'
@@ -143,8 +145,14 @@ export function UploadInput(props: UploadInputProps) {
     collectionSlugs: typeof relationTo === 'string' ? [relationTo] : relationTo,
     filterOptions,
   })
+  const [
+    CreateDocDrawer,
+    _,
+    { closeDrawer: closeCreateDocDrawer, openDrawer: openCreateDocDrawer },
+  ] = useDocumentDrawer({
+    collectionSlug: activeRelationTo,
+  })
 
-  const inputRef = React.useRef<HTMLInputElement>(null)
   const loadedValueDocsRef = React.useRef<boolean>(false)
 
   const canCreate = useMemo(() => {
@@ -242,7 +250,7 @@ export function UploadInput(props: UploadInputProps) {
     [value, onChange, activeRelationTo, hasMany],
   )
 
-  const onFileSelection = React.useCallback(
+  const onLocalFileSelection = React.useCallback(
     (fileList?: FileList) => {
       let fileListToUse = fileList
       if (!hasMany && fileList && fileList.length > 1) {
@@ -295,6 +303,24 @@ export function UploadInput(props: UploadInputProps) {
     [activeRelationTo, closeListDrawer, onChange, populateDocs, value],
   )
 
+  const onDocCreate = React.useCallback(
+    (data) => {
+      if (data.doc) {
+        setPopulatedDocs((currentDocs) => [
+          ...(currentDocs || []),
+          {
+            relationTo: activeRelationTo,
+            value: data.doc,
+          },
+        ])
+
+        onChange(data.doc.id)
+      }
+      closeCreateDocDrawer()
+    },
+    [closeCreateDocDrawer, activeRelationTo, onChange],
+  )
+
   const onListSelect = React.useCallback<NonNullable<ListDrawerProps['onSelect']>>(
     async ({ collectionSlug, docID }) => {
       const loadedDocs = await populateDocs([docID], collectionSlug)
@@ -445,20 +471,18 @@ export function UploadInput(props: UploadInputProps) {
         ) : null}
 
         {showDropzone ? (
-          <Dropzone multipleFiles={hasMany} onChange={onFileSelection}>
+          <Dropzone multipleFiles={hasMany} onChange={onLocalFileSelection}>
             <div className={`${baseClass}__dropzoneContent`}>
               <div className={`${baseClass}__dropzoneContent__buttons`}>
                 <Button
-                  buttonStyle="icon-label"
+                  buttonStyle="pill"
                   disabled={readOnly || !canCreate}
-                  icon="plus"
-                  iconPosition="left"
                   onClick={() => {
                     if (!readOnly) {
                       if (hasMany) {
-                        onFileSelection()
-                      } else if (inputRef.current) {
-                        inputRef.current.click()
+                        onLocalFileSelection()
+                      } else {
+                        openCreateDocDrawer()
                       }
                     }
                   }}
@@ -466,25 +490,14 @@ export function UploadInput(props: UploadInputProps) {
                 >
                   {t('general:createNew')}
                 </Button>
-                <input
-                  aria-hidden="true"
-                  className={`${baseClass}__hidden-input`}
-                  disabled={readOnly}
-                  hidden
-                  multiple={hasMany}
-                  onChange={(e) => {
-                    if (e.target.files && e.target.files.length > 0) {
-                      onFileSelection(e.target.files)
-                    }
-                  }}
-                  ref={inputRef}
-                  type="file"
-                />
+                <span className={`${baseClass}__dropzoneContent__orText`}>{t('general:or')}</span>
                 <ListDrawerToggler className={`${baseClass}__toggler`} disabled={readOnly}>
-                  <Button buttonStyle="icon-label" el="span" icon="plus" iconPosition="left">
+                  <Button buttonStyle="pill" el="span" size="small">
                     {t('fields:chooseFromExisting')}
                   </Button>
                 </ListDrawerToggler>
+
+                <CreateDocDrawer onSave={onDocCreate} />
                 <ListDrawer
                   enableRowSelections={hasMany}
                   onBulkSelect={onListBulkSelect}
diff --git a/packages/ui/src/fields/Upload/index.scss b/packages/ui/src/fields/Upload/index.scss
index 6db04d8ef..08390c892 100644
--- a/packages/ui/src/fields/Upload/index.scss
+++ b/packages/ui/src/fields/Upload/index.scss
@@ -1,10 +1,6 @@
 @import '../../scss/styles.scss';
 
 .upload {
-  .dropzone {
-    padding-right: var(--base);
-  }
-
   &__dropzoneAndUpload {
     display: flex;
     flex-direction: column;
@@ -19,7 +15,7 @@
 
   &__dropzoneContent__buttons {
     display: flex;
-    gap: var(--base);
+    gap: calc(var(--base) / 2);
     position: relative;
     left: -2px;
 
@@ -31,11 +27,17 @@
       font-weight: 100;
     }
   }
+  
+  &__dropzoneContent__orText {
+    color: var(--theme-elevation-500);
+    text-transform: lowercase;
+  }
 
   &__dragAndDropText {
     margin: 0;
     text-transform: lowercase;
     align-self: center;
+    color: var(--theme-elevation-500);
   }
 
   &__loadingRows {