diff --git a/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreview.java b/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreview.java
index 7784d2ae3..820fdc0e5 100644
--- a/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreview.java
+++ b/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreview.java
@@ -11,7 +11,7 @@ import android.view.LayoutInflater;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.briar.R;
 
-import java.util.List;
+import java.util.Collection;
 
 import static android.content.Context.LAYOUT_INFLATER_SERVICE;
 import static android.support.v4.content.ContextCompat.getColor;
@@ -60,7 +60,7 @@ public class ImagePreview extends ConstraintLayout {
 		this.listener = listener;
 	}
 
-	void showPreview(List<Uri> imageUris) {
+	void showPreview(Collection<Uri> imageUris) {
 		if (listener == null) throw new IllegalStateException();
 		if (imageUris.size() == 1) {
 			LayoutParams params = (LayoutParams) imageList.getLayoutParams();
@@ -71,7 +71,14 @@ public class ImagePreview extends ConstraintLayout {
 		imageList.setAdapter(new ImagePreviewAdapter(imageUris, listener));
 	}
 
+	void removeUri(Uri uri) {
+		ImagePreviewAdapter adapter =
+				(ImagePreviewAdapter) imageList.getAdapter();
+		requireNonNull(adapter).removeUri(uri);
+	}
+
 	interface ImagePreviewListener {
+		void onUriError(Uri uri);
 		void onCancel();
 	}
 
diff --git a/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewAdapter.java b/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewAdapter.java
index 057d6e229..8f9238487 100644
--- a/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewAdapter.java
+++ b/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewAdapter.java
@@ -11,6 +11,8 @@ import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.briar.R;
 import org.briarproject.briar.android.view.ImagePreview.ImagePreviewListener;
 
+import java.util.ArrayList;
+import java.util.Collection;
 import java.util.List;
 
 import static java.util.Objects.requireNonNull;
@@ -23,8 +25,9 @@ class ImagePreviewAdapter extends Adapter<ImagePreviewViewHolder> {
 	@LayoutRes
 	private final int layout;
 
-	public ImagePreviewAdapter(List<Uri> items, ImagePreviewListener listener) {
-		this.items = items;
+	public ImagePreviewAdapter(Collection<Uri> items,
+			ImagePreviewListener listener) {
+		this.items = new ArrayList<>(items);
 		this.listener = listener;
 		this.layout = items.size() == 1 ?
 				R.layout.list_item_image_preview_single :
@@ -35,8 +38,7 @@ class ImagePreviewAdapter extends Adapter<ImagePreviewViewHolder> {
 	public ImagePreviewViewHolder onCreateViewHolder(ViewGroup viewGroup, int type) {
 		View v = LayoutInflater.from(viewGroup.getContext())
 				.inflate(layout, viewGroup, false);
-		return new ImagePreviewViewHolder(v, items.size() == 1,
-				requireNonNull(listener));
+		return new ImagePreviewViewHolder(v, requireNonNull(listener));
 	}
 
 	@Override
@@ -49,4 +51,10 @@ class ImagePreviewAdapter extends Adapter<ImagePreviewViewHolder> {
 		return items.size();
 	}
 
+	void removeUri(Uri uri) {
+		int pos = items.indexOf(uri);
+		items.remove(uri);
+		notifyItemRemoved(pos);
+	}
+
 }
diff --git a/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewViewHolder.java b/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewViewHolder.java
index 9db3ea118..d63569024 100644
--- a/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewViewHolder.java
+++ b/briar-android/src/main/java/org/briarproject/briar/android/view/ImagePreviewViewHolder.java
@@ -8,7 +8,6 @@ import android.support.v7.widget.RecyclerView.ViewHolder;
 import android.view.View;
 import android.widget.ImageView;
 import android.widget.ProgressBar;
-import android.widget.Toast;
 
 import com.bumptech.glide.load.DataSource;
 import com.bumptech.glide.load.engine.GlideException;
@@ -21,7 +20,6 @@ import org.briarproject.briar.android.conversation.glide.GlideApp;
 import org.briarproject.briar.android.view.ImagePreview.ImagePreviewListener;
 
 import static android.view.View.INVISIBLE;
-import static android.widget.Toast.LENGTH_LONG;
 import static com.bumptech.glide.load.engine.DiskCacheStrategy.NONE;
 import static com.bumptech.glide.load.resource.bitmap.DownsampleStrategy.FIT_CENTER;
 import static com.bumptech.glide.load.resource.drawable.DrawableTransitionOptions.withCrossFade;
@@ -32,16 +30,13 @@ class ImagePreviewViewHolder extends ViewHolder {
 	@DrawableRes
 	private static final int ERROR_RES = R.drawable.ic_image_broken;
 
-	private final boolean single;
 	private final ImagePreviewListener listener;
 
 	private final ImageView imageView;
 	private final ProgressBar progressBar;
 
-	ImagePreviewViewHolder(View v, boolean single,
-			ImagePreviewListener listener) {
+	ImagePreviewViewHolder(View v, ImagePreviewListener listener) {
 		super(v);
-		this.single = single;
 		this.listener = listener;
 		this.imageView = v.findViewById(R.id.imageView);
 		this.progressBar = v.findViewById(R.id.progressBar);
@@ -59,11 +54,8 @@ class ImagePreviewViewHolder extends ViewHolder {
 					public boolean onLoadFailed(@Nullable GlideException e,
 							Object model, Target<Drawable> target,
 							boolean isFirstResource) {
-						if (single) listener.onCancel();
+						listener.onUriError(uri);
 						progressBar.setVisibility(INVISIBLE);
-						Toast.makeText(imageView.getContext(),
-								R.string.image_attach_error, LENGTH_LONG)
-								.show();
 						return false;
 					}
 
diff --git a/briar-android/src/main/java/org/briarproject/briar/android/view/TextAttachmentController.java b/briar-android/src/main/java/org/briarproject/briar/android/view/TextAttachmentController.java
index 939d0d045..4ebae76db 100644
--- a/briar-android/src/main/java/org/briarproject/briar/android/view/TextAttachmentController.java
+++ b/briar-android/src/main/java/org/briarproject/briar/android/view/TextAttachmentController.java
@@ -5,12 +5,13 @@ import android.content.Intent;
 import android.net.Uri;
 import android.os.Parcel;
 import android.os.Parcelable;
-import android.support.annotation.NonNull;
 import android.support.annotation.Nullable;
 import android.support.annotation.UiThread;
 import android.support.v4.view.AbsSavedState;
 import android.support.v7.widget.AppCompatImageButton;
+import android.widget.Toast;
 
+import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.briar.R;
 import org.briarproject.briar.android.view.ImagePreview.ImagePreviewListener;
 
@@ -26,11 +27,12 @@ import static android.support.v4.view.AbsSavedState.EMPTY_STATE;
 import static android.view.View.GONE;
 import static android.view.View.INVISIBLE;
 import static android.view.View.VISIBLE;
+import static android.widget.Toast.LENGTH_LONG;
 import static java.util.Collections.emptyList;
-import static java.util.Collections.singletonList;
 import static java.util.Objects.requireNonNull;
 
 @UiThread
+@NotNullByDefault
 public class TextAttachmentController extends TextSendController
 		implements ImagePreviewListener {
 
@@ -88,7 +90,8 @@ public class TextAttachmentController extends TextSendController
 	public void onImageReceived(@Nullable Intent resultData) {
 		if (resultData == null) return;
 		if (resultData.getData() != null) {
-			imageUris = singletonList(resultData.getData());
+			imageUris = new ArrayList<>(1);
+			imageUris.add(resultData.getData());
 			onNewUris();
 		} else if (SDK_INT >= 18 && resultData.getClipData() != null) {
 			ClipData clipData = resultData.getClipData();
@@ -162,13 +165,22 @@ public class TextAttachmentController extends TextSendController
 
 	@Override
 	@Nullable
-	public Parcelable onRestoreInstanceState(@NonNull Parcelable inState) {
+	public Parcelable onRestoreInstanceState(Parcelable inState) {
 		SavedState state = (SavedState) inState;
-		imageUris = state.imageUris;
+		imageUris = requireNonNull(state.imageUris);
 		onNewUris();
 		return state.getSuperState();
 	}
 
+	@Override
+	public void onUriError(Uri uri) {
+		imageUris.remove(uri);
+		imagePreview.removeUri(uri);
+		if (imageUris.isEmpty()) onCancel();
+		Toast.makeText(textInput.getContext(), R.string.image_attach_error,
+				LENGTH_LONG).show();
+	}
+
 	@Override
 	public void onCancel() {
 		textInput.clearText();
@@ -176,6 +188,7 @@ public class TextAttachmentController extends TextSendController
 	}
 
 	private static class SavedState extends AbsSavedState {
+		@Nullable
 		private List<Uri> imageUris;
 
 		private SavedState(Parcelable superState) {