diff --git a/functionality/filesharing/filesharing_functionality.go b/functionality/filesharing/filesharing_functionality.go
index c767352..8d76ddf 100644
--- a/functionality/filesharing/filesharing_functionality.go
+++ b/functionality/filesharing/filesharing_functionality.go
@@ -8,12 +8,16 @@ import (
 	"fmt"
 	"io"
 	"math"
+	"os"
 	path "path/filepath"
+	"regexp"
 	"strconv"
+	"strings"
 	"time"
 
 	"cwtch.im/cwtch/model"
 	"cwtch.im/cwtch/model/attr"
+	"cwtch.im/cwtch/model/constants"
 	"cwtch.im/cwtch/peer"
 	"cwtch.im/cwtch/protocol/files"
 	"git.openprivacy.ca/openprivacy/log"
@@ -26,12 +30,20 @@ type Functionality struct {
 // FunctionalityGate returns filesharing if enabled in the given experiment map
 // Note: Experiment maps are currently in libcwtch-go
 func FunctionalityGate(experimentMap map[string]bool) (*Functionality, error) {
-	if experimentMap["filesharing"] {
+	if experimentMap[constants.FileSharingExperiment] {
 		return new(Functionality), nil
 	}
 	return nil, errors.New("filesharing is not enabled")
 }
 
+// PreviewFunctionalityGate returns filesharing if image previews are enabled
+func PreviewFunctionalityGate(experimentMap map[string]bool) (*Functionality, error) {
+	if experimentMap[constants.FileSharingExperiment] && experimentMap[constants.ImagePreviewsExperiment] {
+		return new(Functionality), nil
+	}
+	return nil, errors.New("image previews are not enabled")
+}
+
 // OverlayMessage presents the canonical format of the File Sharing functionality Overlay Message
 // This is the format that the UI will parse to display the message
 type OverlayMessage struct {
@@ -41,6 +53,25 @@ type OverlayMessage struct {
 	Size  uint64 `json:"s"`
 }
 
+// FileKey is the unique reference to a file offer
+func (om *OverlayMessage) FileKey() string {
+	return fmt.Sprintf("%s.%s", om.Hash, om.Nonce)
+}
+
+// ShouldAutoDL checks file size and file name. *DOES NOT* check user settings or contact state
+func (om *OverlayMessage) ShouldAutoDL() bool {
+	if om.Size > constants.ImagePreviewMaxSizeInBytes {
+		return false
+	}
+	lname := strings.ToLower(om.Name)
+	for _, s := range constants.AutoDLFileExts {
+		if strings.HasSuffix(lname, s) {
+			return true
+		}
+	}
+	return false
+}
+
 // DownloadFile given a profile, a conversation handle and a file sharing key, start off a download process
 // to downloadFilePath
 func (f *Functionality) DownloadFile(profile peer.CwtchPeer, conversationID int, downloadFilePath string, manifestFilePath string, key string) {
@@ -103,3 +134,44 @@ func (f *Functionality) ShareFile(filepath string, profile peer.CwtchPeer, conve
 
 	return nil
 }
+
+// GenerateDownloadPath creates a file path that doesn't currently exist on the filesystem
+func GenerateDownloadPath(basePath, fileName string) (filePath, manifestPath string) {
+	// avoid all kina funky shit
+	re := regexp.MustCompile(`[^A-Za-z0-9._-]`)
+	filePath = re.ReplaceAllString(filePath, "")
+	// avoid hidden files on linux
+	for strings.HasPrefix(filePath, ".") {
+		filePath = strings.TrimPrefix(filePath, ".")
+	}
+	// avoid empties
+	if strings.TrimSpace(filePath) == "" {
+		filePath = "untitled"
+	}
+	// if you like it, put a / on it
+	if !strings.HasSuffix(basePath, string(os.PathSeparator)) {
+		basePath = fmt.Sprintf("%s%s", basePath, string(os.PathSeparator))
+	}
+	filePath = fmt.Sprintf("%s%s", basePath, fileName)
+	manifestPath = fmt.Sprintf("%s.manifest", filePath)
+
+	// if file is named "file", iterate "file", "file (2)", "file (3)", ... until DNE
+	// if file is named "file.ext", iterate "file.ext", "file (2).ext", "file (3).ext", ... until DNE
+	parts := strings.Split(fileName, ".")
+	fileNameBase := parts[0]
+	fileNameExt := ""
+	if len(parts) > 1 {
+		fileNameBase = strings.Join(parts[0:len(parts)-1], ".")
+		fileNameExt = fmt.Sprintf(".%s", parts[len(parts)-1])
+	}
+
+	for i := 2; ; i++ {
+		if _, err := os.Open(filePath); os.IsNotExist(err) {
+			if _, err := os.Open(manifestPath); os.IsNotExist(err) {
+				return
+			}
+		}
+		filePath = fmt.Sprintf("%s%s (%d)%s", basePath, fileNameBase, i, fileNameExt)
+		manifestPath = fmt.Sprintf("%s.manifest", filePath)
+	}
+}
diff --git a/model/constants/experiments.go b/model/constants/experiments.go
new file mode 100644
index 0000000..665a856
--- /dev/null
+++ b/model/constants/experiments.go
@@ -0,0 +1,14 @@
+package constants
+
+// FileSharingExperiment Allows file sharing
+const FileSharingExperiment = "filesharing"
+
+// ImagePreviewsExperiment Causes images (up to ImagePreviewMaxSizeInBytes, from accepted contacts) to auto-dl and preview
+// requires FileSharingExperiment to be enabled
+const ImagePreviewsExperiment = "filesharing-images"
+
+// ImagePreviewMaxSizeInBytes Files up to this size will be autodownloaded using ImagePreviewsExperiment
+const ImagePreviewMaxSizeInBytes = 20971520
+
+// AutoDLFileExts Files with these extensions will be autodownloaded using ImagePreviewsExperiment
+var AutoDLFileExts = [...]string{".jpg", ".jpeg", ".png", ".gif", ".webp", ".bmp"}
diff --git a/testing/filesharing/file_sharing_integration_test.go b/testing/filesharing/file_sharing_integration_test.go
index 5c1bd13..47a604f 100644
--- a/testing/filesharing/file_sharing_integration_test.go
+++ b/testing/filesharing/file_sharing_integration_test.go
@@ -2,6 +2,11 @@ package filesharing
 
 import (
 	"crypto/rand"
+	"encoding/base64"
+	"encoding/hex"
+	"encoding/json"
+	"fmt"
+
 	app2 "cwtch.im/cwtch/app"
 	"cwtch.im/cwtch/app/utils"
 	"cwtch.im/cwtch/event"
@@ -12,14 +17,10 @@ import (
 	"cwtch.im/cwtch/peer"
 	"cwtch.im/cwtch/protocol/connections"
 	"cwtch.im/cwtch/protocol/files"
-	"encoding/base64"
-	"encoding/hex"
-	"encoding/json"
-	"fmt"
 	"git.openprivacy.ca/openprivacy/connectivity/tor"
 	"git.openprivacy.ca/openprivacy/log"
+
 	// Import SQL Cipher
-	_ "github.com/mutecomm/go-sqlcipher/v4"
 	mrand "math/rand"
 	"os"
 	"os/user"
@@ -28,6 +29,8 @@ import (
 	"runtime/pprof"
 	"testing"
 	"time"
+
+	_ "github.com/mutecomm/go-sqlcipher/v4"
 )
 
 func waitForPeerPeerConnection(t *testing.T, peera peer.CwtchPeer, peerb peer.CwtchPeer) {
@@ -121,7 +124,7 @@ func TestFileSharing(t *testing.T) {
 
 	fmt.Println("Alice and Bob are Connected!!")
 
-	filesharingFunctionality, _ := filesharing.FunctionalityGate(map[string]bool{"filesharing": true})
+	filesharingFunctionality, _ := filesharing.FunctionalityGate(map[string]bool{constants.FileSharingExperiment: true})
 
 	err = filesharingFunctionality.ShareFile("cwtch.png", alice, 1)