diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java b/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java
index f6745af24..a256d91ff 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/Database.java
@@ -68,6 +68,13 @@ interface Database<T> {
 	 */
 	void close() throws DbException;
 
+	/**
+	 * Returns true if the dirty flag was set while opening the database,
+	 * indicating that the database has not been shut down properly the last
+	 * time it was closed and some data could be lost.
+	 */
+	boolean wasDirtyOnInitialisation();
+
 	/**
 	 * Starts a new transaction and returns an object representing it.
 	 */
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseConstants.java b/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseConstants.java
index f27d45ced..11e4ba64c 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseConstants.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/DatabaseConstants.java
@@ -37,4 +37,10 @@ interface DatabaseConstants {
 	 * has passed since the last compaction.
 	 */
 	long MAX_COMPACTION_INTERVAL_MS = DAYS.toMillis(30);
+
+	/**
+	 * The {@link Settings} key under which the flag is stored indicating
+	 * whether the database is marked as dirty.
+	 */
+	String DIRTY_KEY = "dirty";
 }
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/H2Database.java b/bramble-core/src/main/java/org/briarproject/bramble/db/H2Database.java
index fe59c35a1..ce4433005 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/H2Database.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/H2Database.java
@@ -84,9 +84,14 @@ class H2Database extends JdbcDatabase {
 	@Override
 	public void close() throws DbException {
 		// H2 will close the database when the last connection closes
+		Connection c = null;
 		try {
+			c = createConnection();
 			super.closeAllConnections();
+			setDirty(c, false);
+			c.close();
 		} catch (SQLException e) {
+			tryToClose(c, LOG, WARNING);
 			throw new DbException(e);
 		}
 	}
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/HyperSqlDatabase.java b/bramble-core/src/main/java/org/briarproject/bramble/db/HyperSqlDatabase.java
index aad359498..bdc985ed0 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/HyperSqlDatabase.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/HyperSqlDatabase.java
@@ -81,6 +81,7 @@ class HyperSqlDatabase extends JdbcDatabase {
 		try {
 			super.closeAllConnections();
 			c = createConnection();
+			setDirty(c, false);
 			s = c.createStatement();
 			s.executeQuery("SHUTDOWN");
 			s.close();
diff --git a/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java b/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java
index c56b48e8d..b559b2924 100644
--- a/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java
+++ b/bramble-core/src/main/java/org/briarproject/bramble/db/JdbcDatabase.java
@@ -81,6 +81,7 @@ import static org.briarproject.bramble.api.sync.validation.MessageState.DELIVERE
 import static org.briarproject.bramble.api.sync.validation.MessageState.PENDING;
 import static org.briarproject.bramble.api.sync.validation.MessageState.UNKNOWN;
 import static org.briarproject.bramble.db.DatabaseConstants.DB_SETTINGS_NAMESPACE;
+import static org.briarproject.bramble.db.DatabaseConstants.DIRTY_KEY;
 import static org.briarproject.bramble.db.DatabaseConstants.LAST_COMPACTED_KEY;
 import static org.briarproject.bramble.db.DatabaseConstants.MAX_COMPACTION_INTERVAL_MS;
 import static org.briarproject.bramble.db.DatabaseConstants.SCHEMA_VERSION_KEY;
@@ -354,9 +355,14 @@ abstract class JdbcDatabase implements Database<Connection> {
 	@GuardedBy("connectionsLock")
 	private boolean closed = false;
 
+	private volatile boolean wasDirtyOnInitialisation = false;
+
 	protected abstract Connection createConnection()
 			throws DbException, SQLException;
 
+	// Used exclusively during open to compact the database after schema
+	// migrations or after DatabaseConstants#MAX_COMPACTION_INTERVAL_MS has
+	// elapsed
 	protected abstract void compactAndClose() throws DbException;
 
 	JdbcDatabase(DatabaseTypes databaseTypes, MessageFactory messageFactory,
@@ -381,13 +387,19 @@ abstract class JdbcDatabase implements Database<Connection> {
 		try {
 			if (reopen) {
 				Settings s = getSettings(txn, DB_SETTINGS_NAMESPACE);
+				wasDirtyOnInitialisation = isDirty(s);
 				compact = migrateSchema(txn, s, listener) || isCompactionDue(s);
 			} else {
+				wasDirtyOnInitialisation = false;
 				createTables(txn);
 				initialiseSettings(txn);
 				compact = false;
 			}
+			if (LOG.isLoggable(INFO)) {
+				LOG.info("db dirty? " + wasDirtyOnInitialisation);
+			}
 			createIndexes(txn);
+			setDirty(txn, true);
 			commitTransaction(txn);
 		} catch (DbException e) {
 			abortTransaction(txn);
@@ -414,6 +426,11 @@ abstract class JdbcDatabase implements Database<Connection> {
 		}
 	}
 
+	@Override
+	public boolean wasDirtyOnInitialisation() {
+		return wasDirtyOnInitialisation;
+	}
+
 	/**
 	 * Compares the schema version stored in the database with the schema
 	 * version used by the current code and applies any suitable migrations to
@@ -488,6 +505,16 @@ abstract class JdbcDatabase implements Database<Connection> {
 		mergeSettings(txn, s, DB_SETTINGS_NAMESPACE);
 	}
 
+	private boolean isDirty(Settings s) {
+		return s.getBoolean(DIRTY_KEY, false);
+	}
+
+	protected void setDirty(Connection txn, boolean dirty) throws DbException {
+		Settings s = new Settings();
+		s.putBoolean(DIRTY_KEY, dirty);
+		mergeSettings(txn, s, DB_SETTINGS_NAMESPACE);
+	}
+
 	private void initialiseSettings(Connection txn) throws DbException {
 		Settings s = new Settings();
 		s.putInt(SCHEMA_VERSION_KEY, CODE_SCHEMA_VERSION);
diff --git a/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java b/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java
index ac4231216..40d9b7059 100644
--- a/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java
+++ b/bramble-core/src/test/java/org/briarproject/bramble/db/JdbcDatabaseTest.java
@@ -41,8 +41,12 @@ import org.junit.Test;
 
 import java.io.File;
 import java.sql.Connection;
+import java.sql.Driver;
+import java.sql.DriverManager;
+import java.sql.SQLException;
 import java.util.ArrayList;
 import java.util.Collection;
+import java.util.Enumeration;
 import java.util.List;
 import java.util.Map;
 import java.util.Map.Entry;
@@ -2347,6 +2351,67 @@ public abstract class JdbcDatabaseTest extends BrambleTestCase {
 		db.close();
 	}
 
+
+	@Test
+	public void testShutdownGracefully() throws Exception {
+		Database<Connection> db = open(false);
+		db.close();
+		open(true);
+		assertFalse(db.wasDirtyOnInitialisation());
+	}
+
+	@Test
+	public void testShutdownDirty() throws Exception {
+		Database<Connection> db = open(false);
+
+		// We want to simulate a dirty shutdown here which would normally be
+		// caused by an empty battery or by force closing the Android app.
+		// As there is no obvious way to simulate this, we're artificially
+		// causing an SqlException during close() here by unloading the JDBC
+		// drivers.
+		List<String> unloadedDrivers = unloadDrivers();
+
+		try {
+			db.close();
+			fail();
+		} catch (Exception e) {
+			// continue
+			e.printStackTrace();
+		}
+
+		// Reloading drivers to continue so that we're able to work with the
+		// database again.
+		reloadDrivers(unloadedDrivers);
+
+		db = open(true);
+		assertTrue(db.wasDirtyOnInitialisation());
+	}
+
+	@Test
+	public void testShutdownDirtyThenGracefully() throws Exception {
+		Database<Connection> db = open(false);
+
+		// Simulating a dirty shutdown here, look at #testShutdownDirty for
+		// details.
+		List<String> unloadedDrivers = unloadDrivers();
+
+		try {
+			db.close();
+			fail();
+		} catch (Exception e) {
+			// continue
+		}
+
+		reloadDrivers(unloadedDrivers);
+
+		db = open(true);
+		assertTrue(db.wasDirtyOnInitialisation());
+
+		db.close();
+		db = open(true);
+		assertFalse(db.wasDirtyOnInitialisation());
+	}
+
 	private Database<Connection> open(boolean resume) throws Exception {
 		return open(resume, new TestMessageFactory(), new SystemClock());
 	}
@@ -2402,6 +2467,31 @@ public abstract class JdbcDatabaseTest extends BrambleTestCase {
 				rootKey, alice);
 	}
 
+	private List<String> unloadDrivers() {
+		Enumeration<Driver> drivers = DriverManager.getDrivers();
+		List<String> unloaded = new ArrayList<>();
+		while (drivers.hasMoreElements()) {
+			Driver d = drivers.nextElement();
+			try {
+				DriverManager.deregisterDriver(d);
+				unloaded.add(d.getClass().getName());
+			} catch (SQLException e) {
+				e.printStackTrace();
+				fail();
+			}
+		}
+		return unloaded;
+	}
+
+	private void reloadDrivers(List<String> unloadedDrivers)
+			throws ClassNotFoundException, IllegalAccessException,
+			InstantiationException, SQLException {
+		for (String driverName : unloadedDrivers) {
+			DriverManager.registerDriver(
+					(Driver) Class.forName(driverName).newInstance());
+		}
+	}
+
 	@After
 	public void tearDown() {
 		deleteTestDirectory(testDir);