diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5be33f04..582f3963 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Add Parcel Layer [#50](https://github.com/azavea/iow-boundary-tool/pull/50)
 - Add distorable reference image layer [#46](https://github.com/azavea/iow-boundary-tool/pull/46)
 - Add Land & water basemap [#48](https://github.com/azavea/iow-boundary-tool/pull/48)
+- Add user reference image upload [#60](https://github.com/azavea/iow-boundary-tool/pull/60)
 
 ### Changed
 
diff --git a/src/app/src/components/Layers/ReferenceImageLayer.js b/src/app/src/components/Layers/ReferenceImageLayer.js
index 1412bd4c..45cf3aa2 100644
--- a/src/app/src/components/Layers/ReferenceImageLayer.js
+++ b/src/app/src/components/Layers/ReferenceImageLayer.js
@@ -1,12 +1,11 @@
-import { useMemo } from 'react';
+import { useCallback, useEffect, useMemo, useRef } from 'react';
 import { useDispatch, useSelector } from 'react-redux';
 
 import L from './L.DistortableImage.Edit.fix';
-import ReferenceImage from '../../img/raleigh_sanborn_map.jpg';
 
-import { useMapLayer } from '../../hooks';
 import { customizePrototypeIcon } from '../../utils';
 import { updateReferenceImage } from '../../store/mapSlice';
+import { useMap } from 'react-leaflet';
 
 customizePrototypeIcon(L.DistortHandle.prototype, 'ref-handle');
 customizePrototypeIcon(L.DragHandle.prototype, 'ref-handle');
@@ -20,21 +19,26 @@ const convertCornerFromStateFormat = corner => ({
     lng: corner[1],
 });
 
-export default function ReferenceImageLayerVisbilityWrapper() {
-    const showLayer = useSelector(state => state.map.referenceImage.visible);
-
-    return showLayer ? <ReferenceImageLayer /> : null;
-}
-
-function ReferenceImageLayer() {
+export default function ReferenceImageLayer() {
     const dispatch = useDispatch();
+    const map = useMap();
+    const referenceImageLayers = useRef({});
 
-    // TODO: Find a way to initialize the image with transparent/outlined enabled
-    const { corners, mode } = useSelector(state => state.map.referenceImage);
+    const images = useSelector(state => state.map.referenceImages);
 
-    const layer = useMemo(
-        () => {
-            const layer = new L.distortableImageOverlay(ReferenceImage, {
+    const visibleImages = useMemo(
+        () =>
+            Object.fromEntries(
+                Object.entries(images).filter(
+                    ([, imageInfo]) => imageInfo.visible
+                )
+            ),
+        [images]
+    );
+
+    const createLayer = useCallback(
+        ({ url, corners, mode }) => {
+            const layer = new L.distortableImageOverlay(url, {
                 actions: [
                     L.DragAction,
                     L.ScaleAction,
@@ -55,9 +59,14 @@ function ReferenceImageLayer() {
             const updateImageHandler = ({ target: layer }) => {
                 dispatch(
                     updateReferenceImage({
-                        corners: layer._corners.map(convertCornerToStateFormat),
-                        mode: layer.editing._mode,
-                        transparent: layer.editing._transparent,
+                        url,
+                        update: {
+                            corners: layer._corners.map(
+                                convertCornerToStateFormat
+                            ),
+                            mode: layer.editing._mode,
+                            transparent: layer.editing._transparent,
+                        },
                     })
                 );
             };
@@ -78,9 +87,12 @@ function ReferenceImageLayer() {
                     if (layer._corners) {
                         dispatch(
                             updateReferenceImage({
-                                corners: layer._corners.map(
-                                    convertCornerToStateFormat
-                                ),
+                                url,
+                                update: {
+                                    corners: layer._corners.map(
+                                        convertCornerToStateFormat
+                                    ),
+                                },
                             })
                         );
                     }
@@ -89,14 +101,41 @@ function ReferenceImageLayer() {
 
             return layer;
         },
-        // TODO: Figure out how to prevent deselect on re-render
-        // eslint-disable-next-line react-hooks/exhaustive-deps
-        [
-            // corners,
-            // mode,
-            dispatch,
-        ]
+        [dispatch]
     );
 
-    useMapLayer(layer);
+    /**
+     * Since the reference image layers are stored in a mutable ref,
+     * they aren't updated when the redux state changes. This useEffect
+     * hook manually performs those updates by listening to changes of
+     * visibleImages.
+     */
+    useEffect(() => {
+        const imageShouldBeAdded = url =>
+            !(url in referenceImageLayers.current);
+
+        const imageShouldBeHidden = url => !(url in visibleImages);
+
+        for (const [url, { corners, mode }] of Object.entries(visibleImages)) {
+            if (imageShouldBeAdded(url)) {
+                referenceImageLayers.current[url] = createLayer({
+                    url,
+                    corners,
+                    mode,
+                });
+
+                map.addLayer(referenceImageLayers.current[url]);
+            }
+        }
+
+        for (const url of Object.keys(referenceImageLayers.current)) {
+            if (imageShouldBeHidden(url)) {
+                if (map.hasLayer(referenceImageLayers.current[url])) {
+                    map.removeLayer(referenceImageLayers.current[url]);
+                }
+
+                delete referenceImageLayers.current[url];
+            }
+        }
+    }, [visibleImages, map, createLayer]);
 }
diff --git a/src/app/src/components/ModalSections/FileUpload.js b/src/app/src/components/ModalSections/FileUpload.js
index 81e04f0d..2097c4f3 100644
--- a/src/app/src/components/ModalSections/FileUpload.js
+++ b/src/app/src/components/ModalSections/FileUpload.js
@@ -7,7 +7,6 @@ import {
     Icon,
     List,
     ListItem,
-    Progress,
     Text,
 } from '@chakra-ui/react';
 import { useNavigate } from 'react-router-dom';
@@ -15,13 +14,14 @@ import { CloudUploadIcon } from '@heroicons/react/outline';
 
 import { convertIndexedObjectToArray } from '../../utils';
 import ModalSection from './ModalSection';
+import { useAddReferenceImage, useFilePicker } from '../../hooks';
+import { useSelector } from 'react-redux';
 
 export default function FileUpload({ PreviousButton }) {
     const navigate = useNavigate();
+    const addReferenceImage = useAddReferenceImage();
 
-    const [files, setFiles] = useState([]);
-
-    const addFiles = newFiles => setFiles(files => [...files, ...newFiles]);
+    const addFiles = newFiles => newFiles.forEach(addReferenceImage);
 
     return (
         <ModalSection
@@ -41,18 +41,18 @@ export default function FileUpload({ PreviousButton }) {
             </Text>
 
             <Flex mt={4} w='100%' grow>
-                <UploadBox setFiles={addFiles} />
-                <FilesBox files={files}></FilesBox>
+                <UploadBox addFiles={addFiles} />
+                <FilesBox />
             </Flex>
         </ModalSection>
     );
 }
 
-function UploadBox({ setFiles }) {
+function UploadBox({ addFiles }) {
     const { hovering, handleUpload, startDrag, endDrag } =
-        useFileUpload(setFiles);
+        useFileUpload(addFiles);
 
-    const openFileDialog = useFilePicker(setFiles);
+    const openFileDialog = useFilePicker(addFiles);
 
     const onLeaveDragBox = event => {
         const enteredElement = event.relatedTarget;
@@ -103,7 +103,7 @@ function UploadBox({ setFiles }) {
                 <Text color='gray.400'>
                     <Bold>Shapefiles:</Bold> .SHP, .SHX and .DBF
                     <br />
-                    <Bold>Other map files:</Bold> PDF, JPEG, PNG, TIFF
+                    <Bold>Other map files:</Bold> JPEG, PNG
                 </Text>
             </Flex>
         </Box>
@@ -154,24 +154,6 @@ function usePreventBackgroundUpload() {
     }, []);
 }
 
-function useFilePicker(onChange) {
-    const openFileDialog = () => {
-        const input = document.createElement('input');
-        input.type = 'file';
-        input.multiple = true;
-        input.onchange = handlePickFiles;
-
-        input.click();
-    };
-
-    const handlePickFiles = event => {
-        onChange(convertIndexedObjectToArray(event.target.files));
-        event.target.remove();
-    };
-
-    return openFileDialog;
-}
-
 function CloudIconWithBackground() {
     return (
         <Flex
@@ -202,8 +184,12 @@ function Bold({ children }) {
     );
 }
 
-function FilesBox({ files }) {
-    if (files.length === 0) return null;
+function FilesBox() {
+    const imageEntries = Object.entries(
+        useSelector(state => state.map.referenceImages)
+    );
+
+    if (imageEntries.length === 0) return null;
 
     return (
         <Box w='50%' pl={4}>
@@ -211,16 +197,11 @@ function FilesBox({ files }) {
                 Uploaded Files
             </Heading>
             <List>
-                {files.map(file => (
-                    <ListItem key={file.name} mb={6}>
+                {imageEntries.map(([url, { name }]) => (
+                    <ListItem key={url} mb={6}>
                         <Text mb={2} p={2} color='gray.700' bg='gray.50'>
-                            {file.name}
+                            {name}
                         </Text>
-                        <Progress
-                            colorScheme='gray'
-                            size='xs'
-                            isIndeterminate
-                        />
                     </ListItem>
                 ))}
             </List>
diff --git a/src/app/src/components/Sidebar.js b/src/app/src/components/Sidebar.js
index 0e670aa3..f1cd1d26 100644
--- a/src/app/src/components/Sidebar.js
+++ b/src/app/src/components/Sidebar.js
@@ -8,6 +8,7 @@ import {
     Icon,
     Text,
     Circle,
+    Tooltip,
 } from '@chakra-ui/react';
 import {
     MenuIcon,
@@ -26,7 +27,8 @@ import {
     toggleLayer,
     toggleReferenceImageVisibility,
 } from '../store/mapSlice';
-import { DATA_LAYERS } from '../constants';
+import { DATA_LAYERS, SIDEBAR_TEXT_TOOLTIP_THRESHOLD } from '../constants';
+import { useAddReferenceImage, useFilePicker } from '../hooks';
 
 const marginLeft = 4;
 
@@ -55,9 +57,10 @@ function TitleBar() {
 
 function ReferenceLayers() {
     const dispatch = useDispatch();
-    const referenceImageVisible = useSelector(
-        state => state.map.referenceImage.visible
-    );
+    const addReferenceImage = useAddReferenceImage();
+    const openFileDialog = useFilePicker(files => files.map(addReferenceImage));
+
+    const images = useSelector(state => state.map.referenceImages);
 
     return (
         <Box ml={marginLeft} mt={6} mb={6}>
@@ -73,14 +76,22 @@ function ReferenceLayers() {
                 variant='button'
                 leftIcon={<Icon as={PlusIcon} />}
                 mb={4}
+                onClick={openFileDialog}
             >
                 Upload file
             </Button>
-            <VisibilityButton
-                visible={referenceImageVisible}
-                onChange={() => dispatch(toggleReferenceImageVisibility())}
-                label='Reference image'
-            />
+            <Flex direction='column' align='flex-start'>
+                {Object.entries(images).map(([url, image]) => (
+                    <VisibilityButton
+                        key={url}
+                        visible={image.visible}
+                        onChange={() =>
+                            dispatch(toggleReferenceImageVisibility(url))
+                        }
+                        label={image.name}
+                    />
+                ))}
+            </Flex>
         </Box>
     );
 }
@@ -137,31 +148,38 @@ function BasemapLayers() {
 
 function VisibilityButton({ label, visible, onChange, disabled = false }) {
     return (
-        <Button
-            mb={1}
-            leftIcon={
-                <Circle
-                    color='white'
-                    bg={visible ? 'gray.500' : 'gray.600'}
-                    mr={2}
-                >
-                    <Icon
-                        as={visible ? EyeIcon : EyeOffIcon}
-                        m={2}
-                        fontSize='lg'
-                        strokeWidth={1}
-                    />
-                </Circle>
-            }
-            onClick={onChange}
-            variant='link'
-            color={visible ? 'gray.300' : 'gray.500'}
-            textDecoration='none'
-            fontWeight={600}
-            disabled={disabled}
+        <Tooltip
+            label={label}
+            bg='gray.500'
+            hasArrow
+            isDisabled={label.length <= SIDEBAR_TEXT_TOOLTIP_THRESHOLD}
         >
-            {label}
-        </Button>
+            <Button
+                mb={1}
+                leftIcon={
+                    <Circle
+                        color='white'
+                        bg={visible ? 'gray.500' : 'gray.600'}
+                        mr={2}
+                    >
+                        <Icon
+                            as={visible ? EyeIcon : EyeOffIcon}
+                            m={2}
+                            fontSize='lg'
+                            strokeWidth={1}
+                        />
+                    </Circle>
+                }
+                onClick={onChange}
+                variant='link'
+                color={visible ? 'gray.300' : 'gray.500'}
+                textDecoration='none'
+                fontWeight={600}
+                disabled={disabled}
+            >
+                {label}
+            </Button>
+        </Tooltip>
     );
 }
 
diff --git a/src/app/src/constants.js b/src/app/src/constants.js
index 6ccca119..27eaac04 100644
--- a/src/app/src/constants.js
+++ b/src/app/src/constants.js
@@ -25,3 +25,5 @@ export const NC_SOUTH = 33.851169;
 
 export const PARCELS_LAYER_URL =
     'https://services.nconemap.gov/secure/rest/services/NC1Map_Parcels/MapServer';
+
+export const SIDEBAR_TEXT_TOOLTIP_THRESHOLD = 30;
diff --git a/src/app/src/hooks.js b/src/app/src/hooks.js
index ef3fd23b..277eddcd 100644
--- a/src/app/src/hooks.js
+++ b/src/app/src/hooks.js
@@ -1,6 +1,12 @@
 import { useCallback, useEffect, useRef, useState } from 'react';
 import { useMap } from 'react-leaflet';
-import { useSelector } from 'react-redux';
+import { useDispatch, useSelector } from 'react-redux';
+
+import { convertIndexedObjectToArray } from './utils';
+import {
+    createDefaultReferenceImage,
+    updateReferenceImage,
+} from './store/mapSlice';
 
 export function useDialogController() {
     const [isOpen, setIsOpen] = useState(false);
@@ -71,3 +77,36 @@ export function useMapLayer(layer) {
 export function useLayerVisibility(layer) {
     return useSelector(state => state.map.layers).includes(layer);
 }
+
+export function useAddReferenceImage() {
+    const dispatch = useDispatch();
+
+    return file => {
+        const url = URL.createObjectURL(file);
+        dispatch(
+            updateReferenceImage({
+                url,
+                update: createDefaultReferenceImage(file.name),
+            })
+        );
+    };
+}
+
+export function useFilePicker(onChange) {
+    const openFileDialog = () => {
+        const input = document.createElement('input');
+        input.type = 'file';
+        input.multiple = true;
+        input.onchange = handlePickFiles;
+        input.accept = 'image/png, image/jpeg, .png, .jpg, .jpeg';
+
+        input.click();
+    };
+
+    const handlePickFiles = event => {
+        onChange(convertIndexedObjectToArray(event.target.files));
+        event.target.remove();
+    };
+
+    return openFileDialog;
+}
diff --git a/src/app/src/store/mapSlice.js b/src/app/src/store/mapSlice.js
index baffe7ae..5e622b33 100644
--- a/src/app/src/store/mapSlice.js
+++ b/src/app/src/store/mapSlice.js
@@ -9,15 +9,18 @@ const initialState = {
     basemapType: 'default',
     geocodeResult: null,
     mapZoom: MAP_INITIAL_ZOOM,
-    referenceImage: {
-        visible: true,
-        corners: null,
-        mode: 'distort',
-        transparent: false,
-        outlined: false,
-    },
+    referenceImages: {},
 };
 
+export const createDefaultReferenceImage = name => ({
+    name,
+    visible: true,
+    corners: null,
+    mode: 'distort',
+    transparent: false,
+    outlined: false,
+});
+
 const DEFAULT_POLYGON = {
     points: [],
     visible: true,
@@ -93,11 +96,15 @@ export const mapSlice = createSlice({
         setMapZoom: (state, { payload: mapZoom }) => {
             state.mapZoom = mapZoom;
         },
-        toggleReferenceImageVisibility: state => {
-            state.referenceImage.visible = !state.referenceImage.visible;
+        toggleReferenceImageVisibility: (state, { payload: url }) => {
+            state.referenceImages[url].visible =
+                !state.referenceImages[url].visible;
         },
-        updateReferenceImage: (state, { payload: update }) => {
-            state.referenceImage = { ...state.referenceImage, ...update };
+        updateReferenceImage: (state, { payload: { url, update } }) => {
+            state.referenceImages[url] = {
+                ...(state.referenceImages?.[url] ?? {}),
+                ...update,
+            };
         },
     },
 });