DO NOT MERGE: Delay sending of attachments.

and display attachments as they arrive while ImageActivity is open.

briar-android/src/androidTestOfficial/java/org/briarproject/briar/android/attachment/AttachmentRetrieverIntegrationTest.java

@@ -13,8 +13,9 @@ import java.util.Random;
 import androidx.test.ext.junit.runners.AndroidJUnit4;
 
 import static androidx.test.InstrumentationRegistry.getContext;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.AVAILABLE;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.ERROR;
 import static org.junit.Assert.assertEquals;
-import static org.junit.Assert.assertFalse;
 import static org.junit.Assert.assertTrue;
 
 @RunWith(AndroidJUnit4.class)
@@ -27,7 +28,7 @@ public class AttachmentRetrieverIntegrationTest {
 
 	private final ImageHelper imageHelper = new ImageHelperImpl();
 	private final AttachmentRetriever retriever =
-			new AttachmentRetrieverImpl(null, dimensions, imageHelper,
+			new AttachmentRetrieverImpl(null, null, dimensions, imageHelper,
 					new ImageSizeCalculator(imageHelper));
 
 	@Test
@@ -35,7 +36,7 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/jpeg");
 		InputStream is = getAssetInputStream("kitten_small.jpg");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(msgId, item.getMessageId());
 		assertEquals(160, item.getWidth());
 		assertEquals(240, item.getHeight());
@@ -43,7 +44,7 @@ public class AttachmentRetrieverIntegrationTest {
 		assertEquals(240, item.getThumbnailHeight());
 		assertEquals("image/jpeg", item.getMimeType());
 		assertJpgOrJpeg(item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -51,7 +52,7 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/jpeg");
 		InputStream is = getAssetInputStream("kitten_original.jpg");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(msgId, item.getMessageId());
 		assertEquals(1728, item.getWidth());
 		assertEquals(2592, item.getHeight());
@@ -59,7 +60,7 @@ public class AttachmentRetrieverIntegrationTest {
 		assertEquals(dimensions.maxHeight, item.getThumbnailHeight());
 		assertEquals("image/jpeg", item.getMimeType());
 		assertJpgOrJpeg(item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -67,7 +68,7 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/png");
 		InputStream is = getAssetInputStream("kitten.png");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(msgId, item.getMessageId());
 		assertEquals(737, item.getWidth());
 		assertEquals(510, item.getHeight());
@@ -75,7 +76,7 @@ public class AttachmentRetrieverIntegrationTest {
 		assertEquals(138, item.getThumbnailHeight());
 		assertEquals("image/png", item.getMimeType());
 		assertEquals("png", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -83,14 +84,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/gif");
 		InputStream is = getAssetInputStream("uber.gif");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(1, item.getWidth());
 		assertEquals(1, item.getHeight());
 		assertEquals(dimensions.minHeight, item.getThumbnailWidth());
 		assertEquals(dimensions.minHeight, item.getThumbnailHeight());
 		assertEquals("image/gif", item.getMimeType());
 		assertEquals("gif", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -98,14 +99,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/jpeg");
 		InputStream is = getAssetInputStream("lottapixel.jpg");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(64250, item.getWidth());
 		assertEquals(64250, item.getHeight());
 		assertEquals(dimensions.maxWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.maxWidth, item.getThumbnailHeight());
 		assertEquals("image/jpeg", item.getMimeType());
 		assertJpgOrJpeg(item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -113,14 +114,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/png");
 		InputStream is = getAssetInputStream("image_io_crash.png");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(1184, item.getWidth());
 		assertEquals(448, item.getHeight());
 		assertEquals(dimensions.maxWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.minHeight, item.getThumbnailHeight());
 		assertEquals("image/png", item.getMimeType());
 		assertEquals("png", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -128,14 +129,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/gif");
 		InputStream is = getAssetInputStream("gimp_crash.gif");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(1, item.getWidth());
 		assertEquals(1, item.getHeight());
 		assertEquals(dimensions.minHeight, item.getThumbnailWidth());
 		assertEquals(dimensions.minHeight, item.getThumbnailHeight());
 		assertEquals("image/gif", item.getMimeType());
 		assertEquals("gif", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -143,14 +144,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/gif");
 		InputStream is = getAssetInputStream("opti_png_afl.gif");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(32, item.getWidth());
 		assertEquals(32, item.getHeight());
 		assertEquals(dimensions.minHeight, item.getThumbnailWidth());
 		assertEquals(dimensions.minHeight, item.getThumbnailHeight());
 		assertEquals("image/gif", item.getMimeType());
 		assertEquals("gif", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -158,8 +159,8 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/jpeg");
 		InputStream is = getAssetInputStream("libraw_error.jpg");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
-		assertTrue(item.hasError());
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
+		assertEquals(ERROR, item.getState());
 	}
 
 	@Test
@@ -167,14 +168,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/gif");
 		InputStream is = getAssetInputStream("animated.gif");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(65535, item.getWidth());
 		assertEquals(65535, item.getHeight());
 		assertEquals(dimensions.maxWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.maxWidth, item.getThumbnailHeight());
 		assertEquals("image/gif", item.getMimeType());
 		assertEquals("gif", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -182,14 +183,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/gif");
 		InputStream is = getAssetInputStream("animated2.gif");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(10000, item.getWidth());
 		assertEquals(10000, item.getHeight());
 		assertEquals(dimensions.maxWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.maxWidth, item.getThumbnailHeight());
 		assertEquals("image/gif", item.getMimeType());
 		assertEquals("gif", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -197,14 +198,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/gif");
 		InputStream is = getAssetInputStream("error_large.gif");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(16384, item.getWidth());
 		assertEquals(16384, item.getHeight());
 		assertEquals(dimensions.maxWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.maxWidth, item.getThumbnailHeight());
 		assertEquals("image/gif", item.getMimeType());
 		assertEquals("gif", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -212,14 +213,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/jpeg");
 		InputStream is = getAssetInputStream("error_high.jpg");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(1, item.getWidth());
 		assertEquals(10000, item.getHeight());
 		assertEquals(dimensions.minWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.maxHeight, item.getThumbnailHeight());
 		assertEquals("image/jpeg", item.getMimeType());
 		assertJpgOrJpeg(item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -227,14 +228,14 @@ public class AttachmentRetrieverIntegrationTest {
 		AttachmentHeader h = new AttachmentHeader(msgId, "image/jpeg");
 		InputStream is = getAssetInputStream("error_wide.jpg");
 		Attachment a = new Attachment(h, is);
-		AttachmentItem item = retriever.getAttachmentItem(a, true);
+		AttachmentItem item = retriever.createAttachmentItem(a, true);
 		assertEquals(1920, item.getWidth());
 		assertEquals(1, item.getHeight());
 		assertEquals(dimensions.maxWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.minHeight, item.getThumbnailHeight());
 		assertEquals("image/jpeg", item.getMimeType());
 		assertJpgOrJpeg(item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	private InputStream getAssetInputStream(String name) throws Exception {

briar-android/src/main/java/org/briarproject/briar/android/attachment/AttachmentCreatorImpl.java

@@ -34,6 +34,7 @@ import androidx.lifecycle.MutableLiveData;
 import static java.util.logging.Level.WARNING;
 import static java.util.logging.Logger.getLogger;
 import static org.briarproject.bramble.util.LogUtils.logException;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.ERROR;
 import static org.briarproject.briar.android.util.UiUtils.observeForeverOnce;
 import static org.briarproject.briar.api.messaging.MessagingConstants.MAX_IMAGE_SIZE;
 
@@ -109,8 +110,8 @@ class AttachmentCreatorImpl implements AttachmentCreator {
 		// get and cache AttachmentItem for ImagePreview
 		try {
 			Attachment a = retriever.getMessageAttachment(h);
-			AttachmentItem item = retriever.getAttachmentItem(a, needsSize);
-			if (item.hasError()) throw new IOException();
+			AttachmentItem item = retriever.createAttachmentItem(a, needsSize);
+			if (item.getState() == ERROR) throw new IOException();
 			AttachmentItemResult itemResult =
 					new AttachmentItemResult(uri, item);
 			itemResults.add(itemResult);
@@ -167,13 +168,6 @@ class AttachmentCreatorImpl implements AttachmentCreator {
 	@Override
 	@UiThread
 	public void onAttachmentsSent(MessageId id) {
-		List<AttachmentItem> items = new ArrayList<>(itemResults.size());
-		for (AttachmentItemResult itemResult : itemResults) {
-			// check if we are trying to send attachment items with errors
-			if (itemResult.getItem() == null) throw new IllegalStateException();
-			items.add(itemResult.getItem());
-		}
-		retriever.cachePut(id, items);
 		resetState();
 	}
 

briar-android/src/main/java/org/briarproject/briar/android/attachment/AttachmentItem.java

@@ -7,24 +7,33 @@ import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.briar.api.messaging.AttachmentHeader;
 
-import java.util.concurrent.atomic.AtomicLong;
-
 import javax.annotation.concurrent.Immutable;
 
 import androidx.annotation.Nullable;
 
+import static java.lang.System.arraycopy;
 import static java.util.Objects.requireNonNull;
+import static org.briarproject.bramble.util.StringUtils.toHexString;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.LOADING;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.MISSING;
 
 @Immutable
 @NotNullByDefault
 public class AttachmentItem implements Parcelable {
 
+	public enum State {
+		LOADING, MISSING, AVAILABLE, ERROR;
+
+		public boolean isFinal() {
+			return this == AVAILABLE || this == ERROR;
+		}
+	}
+
 	private final AttachmentHeader header;
 	private final int width, height;
 	private final String extension;
 	private final int thumbnailWidth, thumbnailHeight;
-	private final boolean hasError;
-	private final long instanceId;
+	private final State state;
 
 	public static final Creator<AttachmentItem> CREATOR =
 			new Creator<AttachmentItem>() {
@@ -39,19 +48,33 @@ public class AttachmentItem implements Parcelable {
 				}
 			};
 
-	private static final AtomicLong NEXT_INSTANCE_ID = new AtomicLong(0);
-
 	AttachmentItem(AttachmentHeader header, int width, int height,
 			String extension, int thumbnailWidth, int thumbnailHeight,
-			boolean hasError) {
+			State state) {
 		this.header = header;
 		this.width = width;
 		this.height = height;
 		this.extension = extension;
 		this.thumbnailWidth = thumbnailWidth;
 		this.thumbnailHeight = thumbnailHeight;
-		this.hasError = hasError;
-		instanceId = NEXT_INSTANCE_ID.getAndIncrement();
+		this.state = state;
+	}
+
+	/**
+	 * Use only for {@link State MISSING} or {@link State LOADING} items.
+	 */
+	AttachmentItem(AttachmentHeader header, int width, int height,
+			State state) {
+		this(header, width, height, "", width, height, state);
+		if (state != MISSING && state != LOADING)
+			throw new IllegalArgumentException();
+	}
+
+	/**
+	 * Use when the item does not need a size.
+	 */
+	AttachmentItem(AttachmentHeader header, String extension, State state) {
+		this(header, 0, 0, extension, 0, 0, state);
 	}
 
 	protected AttachmentItem(Parcel in) {
@@ -64,8 +87,7 @@ public class AttachmentItem implements Parcelable {
 		extension = requireNonNull(in.readString());
 		thumbnailWidth = in.readInt();
 		thumbnailHeight = in.readInt();
-		hasError = in.readByte() != 0;
-		instanceId = in.readLong();
+		state = State.valueOf(requireNonNull(in.readString()));
 		header = new AttachmentHeader(messageId, mimeType);
 	}
 
@@ -101,12 +123,20 @@ public class AttachmentItem implements Parcelable {
 		return thumbnailHeight;
 	}
 
-	public boolean hasError() {
-		return hasError;
+	public State getState() {
+		return state;
 	}
 
-	public String getTransitionName() {
-		return String.valueOf(instanceId);
+	public String getTransitionName(MessageId conversationItemId) {
+		int len = MessageId.LENGTH;
+		byte[] instanceId = new byte[len * 2];
+		arraycopy(header.getMessageId().getBytes(), 0, instanceId, 0, len);
+		arraycopy(conversationItemId.getBytes(), 0, instanceId, len, len);
+		return toHexString(instanceId);
+	}
+
+	boolean hasSize() {
+		return width != 0 && height != 0;
 	}
 
 	@Override
@@ -123,14 +153,15 @@ public class AttachmentItem implements Parcelable {
 		dest.writeString(extension);
 		dest.writeInt(thumbnailWidth);
 		dest.writeInt(thumbnailHeight);
-		dest.writeByte((byte) (hasError ? 1 : 0));
-		dest.writeLong(instanceId);
+		dest.writeString(state.name());
 	}
 
 	@Override
 	public boolean equals(@Nullable Object o) {
 		return o instanceof AttachmentItem &&
-				instanceId == ((AttachmentItem) o).instanceId;
+				header.getMessageId().equals(
+						((AttachmentItem) o).header.getMessageId()
+				);
 	}
 
 }

briar-android/src/main/java/org/briarproject/briar/android/attachment/AttachmentRetriever.java

@@ -1,29 +1,56 @@
 package org.briarproject.briar.android.attachment;
 
+import org.briarproject.bramble.api.db.DatabaseExecutor;
 import org.briarproject.bramble.api.db.DbException;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.briar.api.messaging.Attachment;
 import org.briarproject.briar.api.messaging.AttachmentHeader;
+import org.briarproject.briar.api.messaging.PrivateMessageHeader;
+import org.briarproject.briar.api.messaging.event.AttachmentReceivedEvent;
 
 import java.io.InputStream;
 import java.util.List;
 
-import androidx.annotation.Nullable;
+import androidx.lifecycle.LiveData;
+
 
 @NotNullByDefault
 public interface AttachmentRetriever {
 
-	void cachePut(MessageId messageId, List<AttachmentItem> attachments);
-
-	@Nullable
-	List<AttachmentItem> cacheGet(MessageId messageId);
-
+	@DatabaseExecutor
 	Attachment getMessageAttachment(AttachmentHeader h) throws DbException;
 
+	/**
+	 * Returns a list of observable {@link LiveData}
+	 * that get updated as the state of their {@link AttachmentItem}s changes.
+	 */
+	List<LiveData<AttachmentItem>> getAttachmentItems(
+			PrivateMessageHeader messageHeader);
+
+	/**
+	 * Retrieves item size and adds the item to the cache, if available.
+	 * <p>
+	 * Use this to eagerly load the attachment size before it gets displayed.
+	 * This is needed for messages containing a single attachment.
+	 * Messages with more than one attachment use a standard size.
+	 */
+	@DatabaseExecutor
+	void cacheAttachmentItemWithSize(MessageId conversationMessageId,
+			AttachmentHeader h) throws DbException;
+
 	/**
 	 * Creates an {@link AttachmentItem} from the {@link Attachment}'s
 	 * {@link InputStream} which will be closed when this method returns.
 	 */
-	AttachmentItem getAttachmentItem(Attachment a, boolean needsSize);
+	AttachmentItem createAttachmentItem(Attachment a, boolean needsSize);
+
+	/**
+	 * Loads an {@link AttachmentItem}
+	 * that arrived via an {@link AttachmentReceivedEvent}
+	 * and notifies the associated {@link LiveData}.
+	 */
+	@DatabaseExecutor
+	void loadAttachmentItem(MessageId attachmentId);
+
 }

briar-android/src/main/java/org/briarproject/briar/android/attachment/AttachmentRetrieverImpl.java

@@ -1,25 +1,39 @@
 package org.briarproject.briar.android.attachment;
 
+import org.briarproject.bramble.api.db.DatabaseExecutor;
 import org.briarproject.bramble.api.db.DbException;
+import org.briarproject.bramble.api.db.NoSuchMessageException;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
 import org.briarproject.bramble.api.sync.MessageId;
+import org.briarproject.briar.android.attachment.AttachmentItem.State;
 import org.briarproject.briar.api.messaging.Attachment;
 import org.briarproject.briar.api.messaging.AttachmentHeader;
 import org.briarproject.briar.api.messaging.MessagingManager;
+import org.briarproject.briar.api.messaging.PrivateMessageHeader;
 
 import java.io.BufferedInputStream;
 import java.io.InputStream;
+import java.util.ArrayList;
 import java.util.List;
 import java.util.Map;
 import java.util.concurrent.ConcurrentHashMap;
+import java.util.concurrent.Executor;
 import java.util.logging.Logger;
 
 import javax.inject.Inject;
 
-import androidx.annotation.Nullable;
+import androidx.lifecycle.LiveData;
+import androidx.lifecycle.MutableLiveData;
 
+import static java.util.Objects.requireNonNull;
 import static java.util.logging.Level.WARNING;
 import static java.util.logging.Logger.getLogger;
+import static org.briarproject.bramble.util.IoUtils.tryToClose;
+import static org.briarproject.bramble.util.LogUtils.logException;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.AVAILABLE;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.ERROR;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.LOADING;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.MISSING;
 
 @NotNullByDefault
 class AttachmentRetrieverImpl implements AttachmentRetriever {
@@ -27,6 +41,8 @@ class AttachmentRetrieverImpl implements AttachmentRetriever {
 	private static final Logger LOG =
 			getLogger(AttachmentRetrieverImpl.class.getName());
 
+	@DatabaseExecutor
+	private final Executor dbExecutor;
 	private final MessagingManager messagingManager;
 	private final ImageHelper imageHelper;
 	private final ImageSizeCalculator imageSizeCalculator;
@@ -34,13 +50,17 @@ class AttachmentRetrieverImpl implements AttachmentRetriever {
 	private final int minWidth, maxWidth;
 	private final int minHeight, maxHeight;
 
-	private final Map<MessageId, List<AttachmentItem>> attachmentCache =
-			new ConcurrentHashMap<>();
+	private final Map<MessageId, MutableLiveData<AttachmentItem>>
+			itemsWithSize = new ConcurrentHashMap<>();
+	private final Map<MessageId, MutableLiveData<AttachmentItem>>
+			itemsWithoutSize = new ConcurrentHashMap<>();
 
 	@Inject
-	AttachmentRetrieverImpl(MessagingManager messagingManager,
+	AttachmentRetrieverImpl(@DatabaseExecutor Executor dbExecutor,
+			MessagingManager messagingManager,
 			AttachmentDimensions dimensions, ImageHelper imageHelper,
 			ImageSizeCalculator imageSizeCalculator) {
+		this.dbExecutor = dbExecutor;
 		this.messagingManager = messagingManager;
 		this.imageHelper = imageHelper;
 		this.imageSizeCalculator = imageSizeCalculator;
@@ -52,40 +72,130 @@ class AttachmentRetrieverImpl implements AttachmentRetriever {
 	}
 
 	@Override
-	public void cachePut(MessageId messageId,
-			List<AttachmentItem> attachments) {
-		attachmentCache.put(messageId, attachments);
-	}
-
-	@Override
-	@Nullable
-	public List<AttachmentItem> cacheGet(MessageId messageId) {
-		return attachmentCache.get(messageId);
-	}
-
-	@Override
+	@DatabaseExecutor
 	public Attachment getMessageAttachment(AttachmentHeader h)
 			throws DbException {
 		return messagingManager.getAttachment(h);
 	}
 
 	@Override
-	public AttachmentItem getAttachmentItem(Attachment a, boolean needsSize) {
-		AttachmentHeader h = a.getHeader();
-		if (!needsSize) {
-			String extension =
-					imageHelper.getExtensionFromMimeType(h.getContentType());
-			boolean hasError = false;
-			if (extension == null) {
-				extension = "";
-				hasError = true;
+	public List<LiveData<AttachmentItem>> getAttachmentItems(
+			PrivateMessageHeader messageHeader) {
+		List<AttachmentHeader> headers = messageHeader.getAttachmentHeaders();
+		List<LiveData<AttachmentItem>> items = new ArrayList<>(headers.size());
+		boolean needsSize = headers.size() == 1;
+		for (AttachmentHeader h : headers) {
+			// try cache for existing item live data
+			MutableLiveData<AttachmentItem> liveData;
+			if (needsSize) liveData = itemsWithSize.get(h.getMessageId());
+			else {
+				// try items with size first, as they work as well
+				liveData = itemsWithSize.get(h.getMessageId());
+				if (liveData == null)
+					liveData = itemsWithoutSize.get(h.getMessageId());
 			}
-			return new AttachmentItem(h, 0, 0, extension, 0, 0, hasError);
+
+			// create new live data with LOADING item if cache miss
+			if (liveData == null) {
+				AttachmentItem item = new AttachmentItem(h,
+						defaultSize, defaultSize, LOADING);
+				final MutableLiveData<AttachmentItem> finalLiveData =
+						new MutableLiveData<>(item);
+				// kick-off loading of attachment, will post to live data
+				dbExecutor.execute(
+						() -> loadAttachmentItem(h, needsSize, finalLiveData));
+				// add new LiveData to cache
+				liveData = finalLiveData;
+				if (needsSize) itemsWithSize.put(h.getMessageId(), liveData);
+				else itemsWithoutSize.put(h.getMessageId(), liveData);
+			}
+			items.add(liveData);
+		}
+		return items;
+	}
+
+	@Override
+	@DatabaseExecutor
+	public void cacheAttachmentItemWithSize(MessageId conversationMessageId,
+			AttachmentHeader h) throws DbException {
+		try {
+			Attachment a = messagingManager.getAttachment(h);
+			AttachmentItem item = createAttachmentItem(a, true);
+			MutableLiveData<AttachmentItem> liveData =
+					new MutableLiveData<>(item);
+			itemsWithSize.put(h.getMessageId(), liveData);
+		} catch (NoSuchMessageException e) {
+			LOG.info("Attachment not received yet");
+		}
+	}
+
+	@Override
+	@DatabaseExecutor
+	public void loadAttachmentItem(MessageId attachmentId) {
+		// try to find LiveData for attachment in both caches
+		MutableLiveData<AttachmentItem> liveData;
+		boolean needsSize = true;
+		liveData = itemsWithSize.get(attachmentId);
+		if (liveData == null) {
+			needsSize = false;
+			liveData = itemsWithoutSize.get(attachmentId);
 		}
 
-		InputStream is = new BufferedInputStream(a.getStream());
-		Size size = imageSizeCalculator.getSize(is, h.getContentType());
+		// If no LiveData for the attachment exists,
+		// its message did not yet arrive and we can ignore it for now.
+		if (liveData == null) return;
 
+		// actually load the attachment item
+		AttachmentHeader h = requireNonNull(liveData.getValue()).getHeader();
+		loadAttachmentItem(h, needsSize, liveData);
+	}
+
+	/**
+	 * Loads an {@link AttachmentItem} from the database
+	 * and notifies the given {@link LiveData}.
+	 */
+	@DatabaseExecutor
+	private void loadAttachmentItem(AttachmentHeader h, boolean needsSize,
+			MutableLiveData<AttachmentItem> liveData) {
+		Attachment a;
+		AttachmentItem item;
+		try {
+			a = messagingManager.getAttachment(h);
+			item = createAttachmentItem(a, needsSize);
+		} catch (NoSuchMessageException e) {
+			LOG.info("Attachment not received yet");
+			item = new AttachmentItem(h, defaultSize, defaultSize, MISSING);
+		} catch (DbException e) {
+			logException(LOG, WARNING, e);
+			item = new AttachmentItem(h, "", ERROR);
+		}
+		liveData.postValue(item);
+	}
+
+	@Override
+	public AttachmentItem createAttachmentItem(Attachment a,
+			boolean needsSize) {
+		AttachmentItem item;
+		AttachmentHeader h = a.getHeader();
+		if (needsSize) {
+			InputStream is = new BufferedInputStream(a.getStream());
+			Size size = imageSizeCalculator.getSize(is, h.getContentType());
+			tryToClose(is, LOG, WARNING);
+			item = createAttachmentItem(h, size);
+		} else {
+			String extension =
+					imageHelper.getExtensionFromMimeType(h.getContentType());
+			State state = AVAILABLE;
+			if (extension == null) {
+				extension = "";
+				state = ERROR;
+			}
+			item = new AttachmentItem(h, extension, state);
+		}
+		return item;
+	}
+
+	private AttachmentItem createAttachmentItem(AttachmentHeader h, Size size) {
 		// calculate thumbnail size
 		Size thumbnailSize = new Size(defaultSize, defaultSize, size.mimeType);
 		if (!size.error) {
@@ -104,8 +214,9 @@ class AttachmentRetrieverImpl implements AttachmentRetriever {
 			hasError = true;
 		}
 		if (extension == null) extension = "";
-		return new AttachmentItem(h, size.width, size.height, extension,
-				thumbnailSize.width, thumbnailSize.height, hasError);
+		State state = hasError ? ERROR : AVAILABLE;
+		return new AttachmentItem(h, size.width, size.height,
+				extension, thumbnailSize.width, thumbnailSize.height, state);
 	}
 
 	private Size getThumbnailSize(int width, int height, String mimeType) {

briar-android/src/main/java/org/briarproject/briar/android/attachment/UnavailableItem.java

@@ -0,0 +1,36 @@
+package org.briarproject.briar.android.attachment;
+
+import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
+import org.briarproject.bramble.api.sync.MessageId;
+import org.briarproject.briar.api.messaging.AttachmentHeader;
+
+import javax.annotation.concurrent.Immutable;
+
+@Immutable
+@NotNullByDefault
+class UnavailableItem {
+
+	private final MessageId conversationMessageId;
+	private final AttachmentHeader header;
+	private final boolean needsSize;
+
+	UnavailableItem(MessageId conversationMessageId,
+			AttachmentHeader header, boolean needsSize) {
+		this.conversationMessageId = conversationMessageId;
+		this.header = header;
+		this.needsSize = needsSize;
+	}
+
+	MessageId getConversationMessageId() {
+		return conversationMessageId;
+	}
+
+	AttachmentHeader getHeader() {
+		return header;
+	}
+
+	boolean needsSize() {
+		return needsSize;
+	}
+
+}

briar-android/src/main/java/org/briarproject/briar/android/conversation/ConversationActivity.java

@@ -27,7 +27,6 @@ import org.briarproject.bramble.api.contact.event.ContactRemovedEvent;
 import org.briarproject.bramble.api.db.DatabaseExecutor;
 import org.briarproject.bramble.api.db.DbException;
 import org.briarproject.bramble.api.db.NoSuchContactException;
-import org.briarproject.bramble.api.db.NoSuchMessageException;
 import org.briarproject.bramble.api.event.Event;
 import org.briarproject.bramble.api.event.EventBus;
 import org.briarproject.bramble.api.event.EventListener;
@@ -65,13 +64,13 @@ import org.briarproject.briar.api.client.ProtocolStateException;
 import org.briarproject.briar.api.client.SessionId;
 import org.briarproject.briar.api.conversation.ConversationManager;
 import org.briarproject.briar.api.conversation.ConversationMessageHeader;
+import org.briarproject.briar.api.conversation.ConversationMessageVisitor;
 import org.briarproject.briar.api.conversation.ConversationRequest;
 import org.briarproject.briar.api.conversation.ConversationResponse;
 import org.briarproject.briar.api.conversation.DeletionResult;
 import org.briarproject.briar.api.conversation.event.ConversationMessageReceivedEvent;
 import org.briarproject.briar.api.forum.ForumSharingManager;
 import org.briarproject.briar.api.introduction.IntroductionManager;
-import org.briarproject.briar.api.messaging.Attachment;
 import org.briarproject.briar.api.messaging.AttachmentHeader;
 import org.briarproject.briar.api.messaging.MessagingManager;
 import org.briarproject.briar.api.messaging.PrivateMessageHeader;
@@ -97,6 +96,7 @@ import androidx.appcompat.widget.Toolbar;
 import androidx.core.app.ActivityCompat;
 import androidx.core.app.ActivityOptionsCompat;
 import androidx.core.content.ContextCompat;
+import androidx.lifecycle.LiveData;
 import androidx.lifecycle.Observer;
 import androidx.lifecycle.ViewModelProvider;
 import androidx.lifecycle.ViewModelProviders;
@@ -118,8 +118,6 @@ import static androidx.core.app.ActivityOptionsCompat.makeSceneTransitionAnimati
 import static androidx.core.view.ViewCompat.setTransitionName;
 import static androidx.lifecycle.Lifecycle.State.STARTED;
 import static androidx.recyclerview.widget.SortedList.INVALID_POSITION;
-import static java.util.Collections.emptyList;
-import static java.util.Collections.singletonList;
 import static java.util.Collections.sort;
 import static java.util.Objects.requireNonNull;
 import static java.util.logging.Level.INFO;
@@ -136,6 +134,7 @@ import static org.briarproject.briar.android.activity.RequestCodes.REQUEST_INTRO
 import static org.briarproject.briar.android.conversation.ImageActivity.ATTACHMENTS;
 import static org.briarproject.briar.android.conversation.ImageActivity.ATTACHMENT_POSITION;
 import static org.briarproject.briar.android.conversation.ImageActivity.DATE;
+import static org.briarproject.briar.android.conversation.ImageActivity.ITEM_ID;
 import static org.briarproject.briar.android.conversation.ImageActivity.NAME;
 import static org.briarproject.briar.android.util.UiUtils.getAvatarTransitionName;
 import static org.briarproject.briar.android.util.UiUtils.getBulbTransitionName;
@@ -185,8 +184,6 @@ public class ConversationActivity extends BriarActivity
 	volatile GroupInvitationManager groupInvitationManager;
 
 	private final Map<MessageId, String> textCache = new ConcurrentHashMap<>();
-	private final Map<MessageId, PrivateMessageHeader> missingAttachments =
-			new ConcurrentHashMap<>();
 	private final Observer<String> contactNameObserver = name -> {
 		requireNonNull(name);
 		loadMessages();
@@ -264,6 +261,7 @@ public class ConversationActivity extends BriarActivity
 		adapter = new ConversationAdapter(this, this);
 		list = findViewById(R.id.conversationView);
 		layoutManager = new LinearLayoutManager(this);
+		layoutManager.setStackFromEnd(true);
 		list.setLayoutManager(layoutManager);
 		list.setAdapter(adapter);
 		list.setEmptyText(getString(R.string.no_private_messages));
@@ -540,6 +538,7 @@ public class ConversationActivity extends BriarActivity
 		});
 	}
 
+	@DatabaseExecutor
 	private void eagerlyLoadMessageSize(PrivateMessageHeader h) {
 		try {
 			MessageId id = h.getId();
@@ -556,21 +555,11 @@ public class ConversationActivity extends BriarActivity
 			// images we use a grid so the size is fixed
 			List<AttachmentHeader> headers = h.getAttachmentHeaders();
 			if (headers.size() == 1) {
-				List<AttachmentItem> items = attachmentRetriever.cacheGet(id);
-				if (items == null) {
-					LOG.info("Eagerly loading image size for latest message");
-					AttachmentHeader header = headers.get(0);
-					try {
-						Attachment a = attachmentRetriever
-								.getMessageAttachment(header);
-						AttachmentItem item =
-								attachmentRetriever.getAttachmentItem(a, true);
-						attachmentRetriever.cachePut(id, singletonList(item));
-					} catch (NoSuchMessageException e) {
-						LOG.info("Attachment not received yet");
-						missingAttachments.put(header.getMessageId(), h);
-					}
-				}
+				LOG.info("Eagerly loading image size for latest message");
+				AttachmentHeader header = headers.get(0);
+				// get the item to retrieve its size
+				attachmentRetriever
+						.cacheAttachmentItemWithSize(h.getId(), header);
 			}
 		} catch (DbException e) {
 			logException(LOG, WARNING, e);
@@ -651,44 +640,12 @@ public class ConversationActivity extends BriarActivity
 				&& adapter.isScrolledToBottom(layoutManager);
 	}
 
-	private void loadMessageAttachments(PrivateMessageHeader h) {
-		// TODO: Use placeholders for missing/invalid attachments
-		runOnDbThread(() -> {
-			try {
-				// TODO move getting the items off to IoExecutor, if size == 1
-				List<AttachmentHeader> headers = h.getAttachmentHeaders();
-				boolean needsSize = headers.size() == 1;
-				List<AttachmentItem> items = new ArrayList<>(headers.size());
-				for (AttachmentHeader header : headers) {
-					try {
-						Attachment a = attachmentRetriever
-								.getMessageAttachment(header);
-						AttachmentItem item = attachmentRetriever
-								.getAttachmentItem(a, needsSize);
-						items.add(item);
-					} catch (NoSuchMessageException e) {
-						LOG.info("Attachment not received yet");
-						missingAttachments.put(header.getMessageId(), h);
-						return;
-					}
-				}
-				// Don't cache items unless all are present and valid
-				attachmentRetriever.cachePut(h.getId(), items);
-				displayMessageAttachments(h.getId(), items);
-			} catch (DbException e) {
-				logException(LOG, WARNING, e);
-			}
-		});
-	}
-
-	private void displayMessageAttachments(MessageId m,
-			List<AttachmentItem> items) {
+	private void updateMessageAttachment(MessageId m, AttachmentItem item) {
 		runOnUiThreadUnlessDestroyed(() -> {
 			Pair<Integer, ConversationMessageItem> pair =
 					adapter.getMessageItem(m);
-			if (pair != null) {
+			if (pair != null && pair.getSecond().updateAttachments(item)) {
 				boolean scroll = shouldScrollWhenUpdatingMessage();
-				pair.getSecond().setAttachments(items);
 				adapter.notifyItemChanged(pair.getFirst());
 				if (scroll) scrollToBottom();
 			}
@@ -765,11 +722,8 @@ public class ConversationActivity extends BriarActivity
 
 	@UiThread
 	private void onAttachmentReceived(MessageId attachmentId) {
-		PrivateMessageHeader h = missingAttachments.remove(attachmentId);
-		if (h != null) {
-			LOG.info("Missing attachment received");
-			loadMessageAttachments(h);
-		}
+		runOnDbThread(
+				() -> attachmentRetriever.loadAttachmentItem(attachmentId));
 	}
 
 	@UiThread
@@ -780,7 +734,7 @@ public class ConversationActivity extends BriarActivity
 			observeOnce(viewModel.getContactDisplayName(), this,
 					name -> addConversationItem(h.accept(visitor)));
 		} else {
-			// visitor also loads message text (if existing)
+			// visitor also loads message text and attachments (if existing)
 			addConversationItem(h.accept(visitor));
 		}
 	}
@@ -1107,8 +1061,9 @@ public class ConversationActivity extends BriarActivity
 		i.putExtra(ATTACHMENT_POSITION, attachments.indexOf(item));
 		i.putExtra(NAME, name);
 		i.putExtra(DATE, messageItem.getTime());
+		i.putExtra(ITEM_ID, messageItem.getId().getBytes());
 		// restoring list position should not trigger android bug #224270
-		String transitionName = item.getTransitionName();
+		String transitionName = item.getTransitionName(messageItem.getId());
 		ActivityOptionsCompat options =
 				makeSceneTransitionAnimation(this, view, transitionName);
 		ActivityCompat.startActivity(this, i, options.toBundle());
@@ -1147,15 +1102,37 @@ public class ConversationActivity extends BriarActivity
 		return text;
 	}
 
+	/**
+	 * Called by {@link PrivateMessageHeader#accept(ConversationMessageVisitor)}
+	 */
 	@Override
 	public List<AttachmentItem> getAttachmentItems(PrivateMessageHeader h) {
-		List<AttachmentItem> attachments =
-				attachmentRetriever.cacheGet(h.getId());
-		if (attachments == null) {
-			loadMessageAttachments(h);
-			return emptyList();
+		List<LiveData<AttachmentItem>> liveDataList =
+				attachmentRetriever.getAttachmentItems(h);
+		List<AttachmentItem> items = new ArrayList<>(liveDataList.size());
+		for (LiveData<AttachmentItem> liveData : liveDataList) {
+			liveData.observe(this, new AttachmentObserver(h.getId(), liveData));
+			items.add(requireNonNull(liveData.getValue()));
+		}
+		return items;
+	}
+
+	private class AttachmentObserver implements Observer<AttachmentItem> {
+		private final MessageId conversationMessageId;
+		private final LiveData<AttachmentItem> liveData;
+
+		private AttachmentObserver(MessageId conversationMessageId,
+				LiveData<AttachmentItem> liveData) {
+			this.conversationMessageId = conversationMessageId;
+			this.liveData = liveData;
+		}
+
+		@Override
+		public void onChanged(AttachmentItem attachmentItem) {
+			updateMessageAttachment(conversationMessageId, attachmentItem);
+			if (attachmentItem.getState().isFinal())
+				liveData.removeObserver(this);
 		}
-		return attachments;
 	}
 
 }

briar-android/src/main/java/org/briarproject/briar/android/conversation/ConversationMessageItem.java

@@ -9,12 +9,13 @@ import java.util.List;
 import javax.annotation.concurrent.NotThreadSafe;
 
 import androidx.annotation.LayoutRes;
+import androidx.annotation.UiThread;
 
 @NotThreadSafe
 @NotNullByDefault
 class ConversationMessageItem extends ConversationItem {
 
-	private List<AttachmentItem> attachments;
+	private final List<AttachmentItem> attachments;
 
 	ConversationMessageItem(@LayoutRes int layoutRes, PrivateMessageHeader h,
 			List<AttachmentItem> attachments) {
@@ -26,8 +27,14 @@ class ConversationMessageItem extends ConversationItem {
 		return attachments;
 	}
 
-	void setAttachments(List<AttachmentItem> attachments) {
-		this.attachments = attachments;
+	@UiThread
+	boolean updateAttachments(AttachmentItem item) {
+		int pos = attachments.indexOf(item);
+		if (pos != -1 && attachments.get(pos).getState() != item.getState()) {
+			attachments.set(pos, item);
+			return true;
+		}
+		return false;
 	}
 
 }

briar-android/src/main/java/org/briarproject/briar/android/conversation/ImageActivity.java

@@ -17,6 +17,7 @@ import com.google.android.material.appbar.AppBarLayout;
 
 import org.briarproject.bramble.api.nullsafety.MethodsNotNullByDefault;
 import org.briarproject.bramble.api.nullsafety.ParametersNotNullByDefault;
+import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.briar.R;
 import org.briarproject.briar.android.activity.ActivityComponent;
 import org.briarproject.briar.android.activity.BriarActivity;
@@ -69,6 +70,7 @@ public class ImageActivity extends BriarActivity
 	final static String ATTACHMENT_POSITION = "position";
 	final static String NAME = "name";
 	final static String DATE = "date";
+	final static String ITEM_ID = "itemId";
 
 	@RequiresApi(api = 16)
 	private final static int UI_FLAGS_DEFAULT =
@@ -82,6 +84,7 @@ public class ImageActivity extends BriarActivity
 	private AppBarLayout appBarLayout;
 	private ViewPager viewPager;
 	private List<AttachmentItem> attachments;
+	private MessageId conversationMessageId;
 
 	@Override
 	public void injectActivity(ActivityComponent component) {
@@ -136,6 +139,7 @@ public class ImageActivity extends BriarActivity
 		String date = formatDateAbsolute(this, time);
 		contactName.setText(name);
 		dateView.setText(date);
+		conversationMessageId = new MessageId(i.getByteArrayExtra(ITEM_ID));
 
 		// Set up image ViewPager
 		viewPager = findViewById(R.id.viewPager);
@@ -325,8 +329,8 @@ public class ImageActivity extends BriarActivity
 
 		@Override
 		public Fragment getItem(int position) {
-			Fragment f = ImageFragment
-					.newInstance(attachments.get(position), isFirst);
+			Fragment f = ImageFragment.newInstance(
+					attachments.get(position), conversationMessageId, isFirst);
 			isFirst = false;
 			return f;
 		}

briar-android/src/main/java/org/briarproject/briar/android/conversation/ImageAdapter.java

@@ -49,7 +49,8 @@ class ImageAdapter extends Adapter<ImageViewHolder> {
 	public ImageViewHolder onCreateViewHolder(ViewGroup viewGroup, int type) {
 		View v = LayoutInflater.from(viewGroup.getContext()).inflate(
 				R.layout.list_item_image, viewGroup, false);
-		return new ImageViewHolder(v, imageSize);
+		requireNonNull(conversationItem);
+		return new ImageViewHolder(v, imageSize, conversationItem.getId());
 	}
 
 	@Override
@@ -58,7 +59,7 @@ class ImageAdapter extends Adapter<ImageViewHolder> {
 		// get item
 		requireNonNull(conversationItem);
 		AttachmentItem item = items.get(position);
-		// set onClick listener
+		// set onClick listener, if not missing or error
 		imageViewHolder.itemView.setOnClickListener(v ->
 				listener.onAttachmentClicked(v, conversationItem, item)
 		);

briar-android/src/main/java/org/briarproject/briar/android/conversation/ImageFragment.java

@@ -15,6 +15,7 @@ import com.bumptech.glide.request.target.Target;
 import com.github.chrisbanes.photoview.PhotoView;
 
 import org.briarproject.bramble.api.nullsafety.MethodsNotNullByDefault;
+import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.briar.R;
 import org.briarproject.briar.android.activity.BaseActivity;
 import org.briarproject.briar.android.attachment.AttachmentItem;
@@ -23,6 +24,7 @@ import org.briarproject.briar.android.conversation.glide.GlideApp;
 import javax.annotation.ParametersAreNonnullByDefault;
 import javax.inject.Inject;
 
+import androidx.annotation.DrawableRes;
 import androidx.annotation.Nullable;
 import androidx.fragment.app.Fragment;
 import androidx.lifecycle.ViewModelProvider;
@@ -32,27 +34,36 @@ import static android.os.Build.VERSION.SDK_INT;
 import static android.widget.ImageView.ScaleType.FIT_START;
 import static com.bumptech.glide.load.engine.DiskCacheStrategy.NONE;
 import static org.briarproject.bramble.api.nullsafety.NullSafety.requireNonNull;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.AVAILABLE;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.ERROR;
 import static org.briarproject.briar.android.conversation.ImageActivity.ATTACHMENT_POSITION;
+import static org.briarproject.briar.android.conversation.ImageActivity.ITEM_ID;
 
 @MethodsNotNullByDefault
 @ParametersAreNonnullByDefault
-public class ImageFragment extends Fragment {
+public class ImageFragment extends Fragment
+		implements RequestListener<Drawable> {
 
 	private final static String IS_FIRST = "isFirst";
+	@DrawableRes
+	private static final int ERROR_RES = R.drawable.ic_image_broken;
 
 	@Inject
 	ViewModelProvider.Factory viewModelFactory;
 
 	private AttachmentItem attachment;
 	private boolean isFirst;
+	private MessageId conversationItemId;
 	private ImageViewModel viewModel;
 	private PhotoView photoView;
 
-	static ImageFragment newInstance(AttachmentItem a, boolean isFirst) {
+	static ImageFragment newInstance(AttachmentItem a,
+			MessageId conversationMessageId, boolean isFirst) {
 		ImageFragment f = new ImageFragment();
 		Bundle args = new Bundle();
 		args.putParcelable(ATTACHMENT_POSITION, a);
 		args.putBoolean(IS_FIRST, isFirst);
+		args.putByteArray(ITEM_ID, conversationMessageId.getBytes());
 		f.setArguments(args);
 		return f;
 	}
@@ -70,6 +81,8 @@ public class ImageFragment extends Fragment {
 		Bundle args = requireNonNull(getArguments());
 		attachment = requireNonNull(args.getParcelable(ATTACHMENT_POSITION));
 		isFirst = args.getBoolean(IS_FIRST);
+		conversationItemId =
+				new MessageId(requireNonNull(args.getByteArray(ITEM_ID)));
 	}
 
 	@Nullable
@@ -82,55 +95,72 @@ public class ImageFragment extends Fragment {
 
 		viewModel = ViewModelProviders.of(requireNonNull(getActivity()),
 				viewModelFactory).get(ImageViewModel.class);
+		viewModel.getOnAttachmentLoaded()
+				.observeEvent(this, this::onAttachmentLoaded);
 
 		photoView = v.findViewById(R.id.photoView);
 		photoView.setScaleLevels(1, 2, 4);
 		photoView.setOnClickListener(view -> viewModel.clickImage());
 
-		// Request Listener
-		RequestListener<Drawable> listener = new RequestListener<Drawable>() {
-
-			@Override
-			public boolean onLoadFailed(@Nullable GlideException e,
-					Object model, Target<Drawable> target,
-					boolean isFirstResource) {
-				if (getActivity() != null && isFirst)
-					getActivity().supportStartPostponedEnterTransition();
-				return false;
-			}
-
-			@Override
-			public boolean onResourceReady(Drawable resource, Object model,
-					Target<Drawable> target, DataSource dataSource,
-					boolean isFirstResource) {
-				if (SDK_INT >= 21 && !(resource instanceof Animatable)) {
-					// set transition name only when not animatable,
-					// because the animation won't start otherwise
-					photoView.setTransitionName(
-							attachment.getTransitionName());
-				}
-				// Move image to the top if overlapping toolbar
-				if (viewModel.isOverlappingToolbar(photoView, resource)) {
-					photoView.setScaleType(FIT_START);
-				}
-				if (getActivity() != null && isFirst) {
-					getActivity().supportStartPostponedEnterTransition();
-				}
-				return false;
-			}
-		};
-
-		// Load Image
-		GlideApp.with(this)
-				.load(attachment)
-				// TODO allow if size < maxTextureSize ?
-//				.override(SIZE_ORIGINAL)
-				.diskCacheStrategy(NONE)
-				.error(R.drawable.ic_image_broken)
-				.addListener(listener)
-				.into(photoView);
+		if (attachment.getState() == AVAILABLE) {
+			loadImage();
+			// postponed transition will be started when Image was loaded
+		} else if (attachment.getState() == ERROR) {
+			photoView.setImageResource(ERROR_RES);
+			startPostponedTransition();
+		} else {
+			photoView.setImageResource(R.drawable.ic_image_missing);
+			startPostponedTransition();
+		}
 
 		return v;
 	}
 
+	private void loadImage() {
+		GlideApp.with(this)
+				.load(attachment)
+				// TODO allow if size < maxTextureSize ?
+//					.override(SIZE_ORIGINAL)
+				.diskCacheStrategy(NONE)
+				.error(ERROR_RES)
+				.addListener(this)
+				.into(photoView);
+	}
+
+	private void onAttachmentLoaded(MessageId messageId) {
+		if (attachment.getMessageId().equals(messageId)) loadImage();
+	}
+
+	@Override
+	public boolean onLoadFailed(@Nullable GlideException e,
+			Object model, Target<Drawable> target,
+			boolean isFirstResource) {
+		startPostponedTransition();
+		return false;
+	}
+
+	@Override
+	public boolean onResourceReady(Drawable resource, Object model,
+			Target<Drawable> target, DataSource dataSource,
+			boolean isFirstResource) {
+		if (SDK_INT >= 21 && !(resource instanceof Animatable)) {
+			// set transition name only when not animatable,
+			// because the animation won't start otherwise
+			photoView.setTransitionName(
+					attachment.getTransitionName(conversationItemId));
+		}
+		// Move image to the top if overlapping toolbar
+		if (viewModel.isOverlappingToolbar(photoView, resource)) {
+			photoView.setScaleType(FIT_START);
+		}
+		startPostponedTransition();
+		return false;
+	}
+
+	private void startPostponedTransition() {
+		if (getActivity() != null && isFirst) {
+			getActivity().supportStartPostponedEnterTransition();
+		}
+	}
+
 }

briar-android/src/main/java/org/briarproject/briar/android/conversation/ImageViewHolder.java

@@ -7,6 +7,7 @@ import android.widget.ImageView;
 import com.bumptech.glide.load.Transformation;
 
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
+import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.briar.R;
 import org.briarproject.briar.android.attachment.AttachmentItem;
 import org.briarproject.briar.android.conversation.glide.BriarImageTransformation;
@@ -18,8 +19,12 @@ import androidx.recyclerview.widget.RecyclerView.ViewHolder;
 import androidx.recyclerview.widget.StaggeredGridLayoutManager.LayoutParams;
 
 import static android.os.Build.VERSION.SDK_INT;
+import static android.widget.ImageView.ScaleType.CENTER_CROP;
+import static android.widget.ImageView.ScaleType.FIT_CENTER;
 import static com.bumptech.glide.load.engine.DiskCacheStrategy.NONE;
 import static com.bumptech.glide.load.resource.drawable.DrawableTransitionOptions.withCrossFade;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.AVAILABLE;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.ERROR;
 
 @NotNullByDefault
 class ImageViewHolder extends ViewHolder {
@@ -29,25 +34,33 @@ class ImageViewHolder extends ViewHolder {
 
 	protected final ImageView imageView;
 	private final int imageSize;
+	private final MessageId conversationItemId;
 
-	ImageViewHolder(View v, int imageSize) {
+	ImageViewHolder(View v, int imageSize, MessageId conversationItemId) {
 		super(v);
 		imageView = v.findViewById(R.id.imageView);
 		this.imageSize = imageSize;
+		this.conversationItemId = conversationItemId;
 	}
 
 	void bind(AttachmentItem attachment, Radii r, boolean single,
 			boolean needsStretch) {
-		if (attachment.hasError()) {
-			GlideApp.with(imageView)
-					.clear(imageView);
-			imageView.setImageResource(ERROR_RES);
-		} else {
-			setImageViewDimensions(attachment, single, needsStretch);
-			loadImage(attachment, r);
-			if (SDK_INT >= 21) {
-				imageView.setTransitionName(attachment.getTransitionName());
+		setImageViewDimensions(attachment, single, needsStretch);
+		if (attachment.getState() != AVAILABLE) {
+			GlideApp.with(imageView).clear(imageView);
+			if (attachment.getState() == ERROR) {
+				imageView.setImageResource(ERROR_RES);
+			} else {
+				imageView.setImageResource(R.drawable.ic_image_missing);
 			}
+			imageView.setScaleType(FIT_CENTER);
+		} else {
+			loadImage(attachment, r);
+			imageView.setScaleType(CENTER_CROP);
+		}
+		if (SDK_INT >= 21) {
+			imageView.setTransitionName(
+					attachment.getTransitionName(conversationItemId));
 		}
 	}
 

briar-android/src/main/java/org/briarproject/briar/android/conversation/ImageViewModel.java

@@ -7,13 +7,18 @@ import android.view.View;
 
 import org.briarproject.bramble.api.db.DatabaseExecutor;
 import org.briarproject.bramble.api.db.DbException;
+import org.briarproject.bramble.api.event.Event;
+import org.briarproject.bramble.api.event.EventBus;
+import org.briarproject.bramble.api.event.EventListener;
 import org.briarproject.bramble.api.lifecycle.IoExecutor;
 import org.briarproject.bramble.api.nullsafety.NotNullByDefault;
+import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.briar.android.attachment.AttachmentItem;
 import org.briarproject.briar.android.viewmodel.LiveEvent;
 import org.briarproject.briar.android.viewmodel.MutableLiveEvent;
 import org.briarproject.briar.api.messaging.Attachment;
 import org.briarproject.briar.api.messaging.MessagingManager;
+import org.briarproject.briar.api.messaging.event.AttachmentReceivedEvent;
 
 import java.io.File;
 import java.io.FileOutputStream;
@@ -41,16 +46,19 @@ import static org.briarproject.bramble.util.IoUtils.copyAndClose;
 import static org.briarproject.bramble.util.LogUtils.logException;
 
 @NotNullByDefault
-public class ImageViewModel extends AndroidViewModel {
+public class ImageViewModel extends AndroidViewModel implements EventListener {
 
 	private static Logger LOG = getLogger(ImageViewModel.class.getName());
 
 	private final MessagingManager messagingManager;
+	private final EventBus eventBus;
 	@DatabaseExecutor
 	private final Executor dbExecutor;
 	@IoExecutor
 	private final Executor ioExecutor;
 
+	private final MutableLiveEvent<MessageId> attachmentLoaded =
+			new MutableLiveEvent<>();
 	/**
 	 * true means there was an error saving the image, false if image was saved.
 	 */
@@ -62,13 +70,34 @@ public class ImageViewModel extends AndroidViewModel {
 
 	@Inject
 	ImageViewModel(Application application,
-			MessagingManager messagingManager,
+			MessagingManager messagingManager, EventBus eventBus,
 			@DatabaseExecutor Executor dbExecutor,
 			@IoExecutor Executor ioExecutor) {
 		super(application);
 		this.messagingManager = messagingManager;
+		this.eventBus = eventBus;
 		this.dbExecutor = dbExecutor;
 		this.ioExecutor = ioExecutor;
+
+		eventBus.addListener(this);
+	}
+
+	@Override
+	protected void onCleared() {
+		super.onCleared();
+		eventBus.removeListener(this);
+	}
+
+	@Override
+	public void eventOccurred(Event e) {
+		if (e instanceof AttachmentReceivedEvent) {
+			attachmentLoaded
+					.postEvent(((AttachmentReceivedEvent) e).getMessageId());
+		}
+	}
+
+	LiveEvent<MessageId> getOnAttachmentLoaded() {
+		return attachmentLoaded;
 	}
 
 	void clickImage() {

briar-android/src/main/res/drawable/ic_image_broken.xml

@@ -1,6 +1,6 @@
 <vector xmlns:android="http://schemas.android.com/apk/res/android"
-        android:width="200dp"
-        android:height="200dp"
+        android:width="115dp"
+        android:height="115dp"
         android:viewportHeight="24.0"
         android:viewportWidth="24.0">
 	<path

briar-android/src/main/res/drawable/ic_image_missing.xml

@@ -0,0 +1,10 @@
+<vector
+	xmlns:android="http://schemas.android.com/apk/res/android"
+	android:width="115dp"
+	android:height="115dp"
+	android:viewportHeight="24.0"
+	android:viewportWidth="24.0">
+	<path
+		android:fillColor="#808080"
+		android:pathData="M21,19V5c0,-1.1 -0.9,-2 -2,-2H5c-1.1,0 -2,0.9 -2,2v14c0,1.1 0.9,2 2,2h14c1.1,0 2,-0.9 2,-2zM8.5,13.5l2.5,3.01L14.5,12l4.5,6H5l3.5,-4.5z"/>
+</vector>

briar-android/src/test/java/org/briarproject/briar/android/attachment/AttachmentRetrieverTest.java

@@ -2,6 +2,7 @@ package org.briarproject.briar.android.attachment;
 
 import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.bramble.test.BrambleMockTestCase;
+import org.briarproject.bramble.test.ImmediateExecutor;
 import org.briarproject.briar.api.messaging.Attachment;
 import org.briarproject.briar.api.messaging.AttachmentHeader;
 import org.briarproject.briar.api.messaging.MessagingManager;
@@ -11,12 +12,13 @@ import org.junit.Test;
 
 import java.io.ByteArrayInputStream;
 import java.io.InputStream;
+import java.util.concurrent.Executor;
 
 import static org.briarproject.bramble.test.TestUtils.getRandomBytes;
 import static org.briarproject.bramble.test.TestUtils.getRandomId;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.AVAILABLE;
+import static org.briarproject.briar.android.attachment.AttachmentItem.State.ERROR;
 import static org.junit.Assert.assertEquals;
-import static org.junit.Assert.assertFalse;
-import static org.junit.Assert.assertTrue;
 
 public class AttachmentRetrieverTest extends BrambleMockTestCase {
 
@@ -33,8 +35,9 @@ public class AttachmentRetrieverTest extends BrambleMockTestCase {
 		MessagingManager messagingManager =
 				context.mock(MessagingManager.class);
 		imageSizeCalculator = context.mock(ImageSizeCalculator.class);
-		retriever = new AttachmentRetrieverImpl(messagingManager, dimensions,
-				imageHelper, imageSizeCalculator);
+		Executor dbExecutor = new ImmediateExecutor();
+		retriever = new AttachmentRetrieverImpl(dbExecutor, messagingManager,
+				dimensions, imageHelper, imageSizeCalculator);
 	}
 
 	@Test
@@ -47,10 +50,10 @@ public class AttachmentRetrieverTest extends BrambleMockTestCase {
 			will(returnValue("jpg"));
 		}});
 
-		AttachmentItem item = retriever.getAttachmentItem(attachment, false);
+		AttachmentItem item = retriever.createAttachmentItem(attachment, false);
 		assertEquals(mimeType, item.getMimeType());
 		assertEquals("jpg", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -63,8 +66,8 @@ public class AttachmentRetrieverTest extends BrambleMockTestCase {
 			will(returnValue(null));
 		}});
 
-		AttachmentItem item = retriever.getAttachmentItem(attachment, false);
-		assertTrue(item.hasError());
+		AttachmentItem item = retriever.createAttachmentItem(attachment, false);
+		assertEquals(ERROR, item.getState());
 	}
 
 	@Test
@@ -80,7 +83,7 @@ public class AttachmentRetrieverTest extends BrambleMockTestCase {
 			will(returnValue("jpg"));
 		}});
 
-		AttachmentItem item = retriever.getAttachmentItem(attachment, true);
+		AttachmentItem item = retriever.createAttachmentItem(attachment, true);
 		assertEquals(msgId, item.getMessageId());
 		assertEquals(160, item.getWidth());
 		assertEquals(240, item.getHeight());
@@ -88,7 +91,7 @@ public class AttachmentRetrieverTest extends BrambleMockTestCase {
 		assertEquals(240, item.getThumbnailHeight());
 		assertEquals(mimeType, item.getMimeType());
 		assertEquals("jpg", item.getExtension());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -104,12 +107,12 @@ public class AttachmentRetrieverTest extends BrambleMockTestCase {
 			will(returnValue("jpg"));
 		}});
 
-		AttachmentItem item = retriever.getAttachmentItem(attachment, true);
+		AttachmentItem item = retriever.createAttachmentItem(attachment, true);
 		assertEquals(1728, item.getWidth());
 		assertEquals(2592, item.getHeight());
 		assertEquals(dimensions.maxWidth, item.getThumbnailWidth());
 		assertEquals(dimensions.maxHeight, item.getThumbnailHeight());
-		assertFalse(item.hasError());
+		assertEquals(AVAILABLE, item.getState());
 	}
 
 	@Test
@@ -125,8 +128,8 @@ public class AttachmentRetrieverTest extends BrambleMockTestCase {
 			will(returnValue(null));
 		}});
 
-		AttachmentItem item = retriever.getAttachmentItem(attachment, true);
-		assertTrue(item.hasError());
+		AttachmentItem item = retriever.createAttachmentItem(attachment, true);
+		assertEquals(ERROR, item.getState());
 	}
 
 	private Attachment getAttachment(String contentType) {

briar-api/src/main/java/org/briarproject/briar/api/messaging/MessagingManager.java

@@ -68,7 +68,7 @@ public interface MessagingManager extends ConversationClient {
 	String getMessageText(MessageId m) throws DbException;
 
 	/**
-	 * Returns the attachment with the given message ID and content type.
+	 * Returns the attachment with the given attachment header.
 	 *
 	 * @throws InvalidAttachmentException If the header refers to a message
 	 * that is not an attachment, or to an attachment that does not have the

briar-core/src/main/java/org/briarproject/briar/messaging/MessagingManagerImpl.java

@@ -25,6 +25,7 @@ import org.briarproject.bramble.api.sync.Message;
 import org.briarproject.bramble.api.sync.MessageId;
 import org.briarproject.bramble.api.sync.MessageStatus;
 import org.briarproject.bramble.api.sync.validation.IncomingMessageHook;
+import org.briarproject.bramble.api.system.Scheduler;
 import org.briarproject.bramble.api.versioning.ClientVersioningManager;
 import org.briarproject.bramble.api.versioning.ClientVersioningManager.ClientVersioningHook;
 import org.briarproject.briar.api.client.MessageTracker;
@@ -52,14 +53,20 @@ import java.util.HashSet;
 import java.util.List;
 import java.util.Map;
 import java.util.Set;
+import java.util.concurrent.ScheduledExecutorService;
+import java.util.logging.Logger;
 
 import javax.annotation.concurrent.Immutable;
 import javax.inject.Inject;
 
 import static java.util.Collections.emptyList;
+import static java.util.concurrent.TimeUnit.SECONDS;
+import static java.util.logging.Level.WARNING;
+import static java.util.logging.Logger.getLogger;
 import static org.briarproject.bramble.api.sync.SyncConstants.MAX_MESSAGE_BODY_LENGTH;
 import static org.briarproject.bramble.api.sync.validation.MessageState.DELIVERED;
 import static org.briarproject.bramble.util.IoUtils.copyAndClose;
+import static org.briarproject.bramble.util.LogUtils.logException;
 import static org.briarproject.briar.client.MessageTrackerConstants.MSG_KEY_READ;
 import static org.briarproject.briar.messaging.MessageTypes.ATTACHMENT;
 import static org.briarproject.briar.messaging.MessageTypes.PRIVATE_MESSAGE;
@@ -78,6 +85,10 @@ class MessagingManagerImpl implements MessagingManager, IncomingMessageHook,
 		ConversationClient, OpenDatabaseHook, ContactHook,
 		ClientVersioningHook {
 
+	private static final Logger LOG =
+			getLogger(MessagingManagerImpl.class.getName());
+
+	private final ScheduledExecutorService scheduler;
 	private final DatabaseComponent db;
 	private final ClientHelper clientHelper;
 	private final MetadataParser metadataParser;
@@ -86,10 +97,12 @@ class MessagingManagerImpl implements MessagingManager, IncomingMessageHook,
 	private final ContactGroupFactory contactGroupFactory;
 
 	@Inject
-	MessagingManagerImpl(DatabaseComponent db, ClientHelper clientHelper,
+	MessagingManagerImpl(@Scheduler ScheduledExecutorService scheduler,
+			DatabaseComponent db, ClientHelper clientHelper,
 			ClientVersioningManager clientVersioningManager,
 			MetadataParser metadataParser, MessageTracker messageTracker,
 			ContactGroupFactory contactGroupFactory) {
+		this.scheduler = scheduler;
 		this.db = db;
 		this.clientHelper = clientHelper;
 		this.metadataParser = metadataParser;
@@ -245,9 +258,20 @@ class MessagingManagerImpl implements MessagingManager, IncomingMessageHook,
 				meta.put(MSG_KEY_ATTACHMENT_HEADERS, headers);
 			}
 			// Mark attachments as shared and permanent now we're ready to send
+			// FIXME: Revert
+			int i = 15;
 			for (AttachmentHeader a : m.getAttachmentHeaders()) {
-				db.setMessageShared(txn, a.getMessageId());
-				db.setMessagePermanent(txn, a.getMessageId());
+				scheduler.schedule(() -> {
+					try {
+						db.transaction(false, txn1 -> {
+							db.setMessageShared(txn1, a.getMessageId());
+							db.setMessagePermanent(txn1, a.getMessageId());
+						});
+					} catch (DbException e) {
+						logException(LOG, WARNING, e);
+					}
+				}, i, SECONDS);
+				i *= 2;
 			}
 			clientHelper.addLocalMessage(txn, m.getMessage(), meta, true,
 					false);