Index: /trunk/src/org/openstreetmap/josm/gui/layer/geoimage/ImageViewerDialog.java
===================================================================
--- /trunk/src/org/openstreetmap/josm/gui/layer/geoimage/ImageViewerDialog.java	(revision 18684)
+++ /trunk/src/org/openstreetmap/josm/gui/layer/geoimage/ImageViewerDialog.java	(revision 18685)
@@ -573,4 +573,28 @@
                     imageEntry.remove();
                 }
+                selectNextImageAfterDeletion(imageEntry);
+            }
+        }
+
+        /**
+         * Select the logical next entry after deleting the currently viewed image
+         * @param oldEntry The image entry that was just deleted
+         */
+        private void selectNextImageAfterDeletion(IImageEntry<?> oldEntry) {
+            final IImageEntry<?> currentImageEntry = ImageViewerDialog.this.currentEntry;
+            // This is mostly just in case something changes the displayed entry (aka avoid race condition) or an image provider
+            // sets the next image itself.
+            if (Objects.equals(currentImageEntry, oldEntry)) {
+                final IImageEntry<?> nextImage;
+                if (oldEntry instanceof ImageEntry) {
+                    nextImage = ((ImageEntry) oldEntry).getDataSet().getSelectedImage();
+                } else if (oldEntry.getNextImage() != null) {
+                    nextImage = oldEntry.getNextImage();
+                } else if (oldEntry.getPreviousImage() != null) {
+                    nextImage = oldEntry.getPreviousImage();
+                } else {
+                    nextImage = null;
+                }
+                ImageViewerDialog.getInstance().displayImages(nextImage == null ? null : Collections.singletonList(nextImage));
             }
         }
@@ -588,7 +612,8 @@
         public void actionPerformed(ActionEvent e) {
             if (currentEntry != null) {
-                List<IImageEntry<?>> toDelete = currentEntry instanceof ImageEntry ?
-                        new ArrayList<>(((ImageEntry) currentEntry).getDataSet().getSelectedImages())
-                        : Collections.singletonList(currentEntry);
+                IImageEntry<?> oldEntry = ImageViewerDialog.this.currentEntry;
+                List<IImageEntry<?>> toDelete = oldEntry instanceof ImageEntry ?
+                        new ArrayList<>(((ImageEntry) oldEntry).getDataSet().getSelectedImages())
+                        : Collections.singletonList(oldEntry);
                 int size = toDelete.size();
 
@@ -631,4 +656,5 @@
                         data.updateSelectedImage();
                     });
+                    ImageViewerDialog.this.imageRemoveAction.selectNextImageAfterDeletion(oldEntry);
                 }
             }
Index: /trunk/test/unit/org/openstreetmap/josm/gui/layer/geoimage/ImageViewerDialogTest.java
===================================================================
--- /trunk/test/unit/org/openstreetmap/josm/gui/layer/geoimage/ImageViewerDialogTest.java	(revision 18685)
+++ /trunk/test/unit/org/openstreetmap/josm/gui/layer/geoimage/ImageViewerDialogTest.java	(revision 18685)
@@ -0,0 +1,96 @@
+// License: GPL. For details, see LICENSE file.
+package org.openstreetmap.josm.gui.layer.geoimage;
+
+import static org.junit.jupiter.api.Assertions.assertEquals;
+import static org.junit.jupiter.api.Assertions.assertNotEquals;
+import static org.junit.jupiter.api.Assertions.assertNull;
+import static org.junit.jupiter.api.Assertions.assertSame;
+
+import java.io.File;
+import java.io.IOException;
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.util.ArrayList;
+import java.util.List;
+import java.util.concurrent.ExecutionException;
+import java.util.concurrent.TimeUnit;
+import java.util.concurrent.TimeoutException;
+
+import javax.swing.Action;
+import javax.swing.JButton;
+import javax.swing.JPanel;
+
+import org.junit.jupiter.api.BeforeEach;
+import org.junit.jupiter.api.extension.RegisterExtension;
+import org.junit.jupiter.api.io.TempDir;
+import org.junit.jupiter.params.ParameterizedTest;
+import org.junit.jupiter.params.provider.ValueSource;
+import org.openstreetmap.josm.TestUtils;
+import org.openstreetmap.josm.data.imagery.street_level.IImageEntry;
+import org.openstreetmap.josm.gui.MainApplication;
+import org.openstreetmap.josm.spi.preferences.Config;
+import org.openstreetmap.josm.testutils.JOSMTestRules;
+import org.openstreetmap.josm.testutils.mockers.ExtendedDialogMocker;
+
+/**
+ * Test class for {@link ImageViewerDialog}
+ */
+class ImageViewerDialogTest {
+    @RegisterExtension
+    static JOSMTestRules rule = new JOSMTestRules().main().projection();
+
+    @TempDir
+    Path tempDirectory;
+
+    private ImageViewerDialog dialog;
+    @BeforeEach
+    void setup() {
+        this.dialog = ImageViewerDialog.getInstance();
+        this.dialog.displayImages(null);
+    }
+
+    /**
+     * Generate a number of image entries
+     * @param numberOfEntries The number of image entries to generate
+     * @return The generated entries
+     * @throws IOException If a file could not be copied to a temp directory
+     */
+    protected List<? extends IImageEntry<?>> generateImageEntries(int numberOfEntries) throws IOException {
+        final List<ImageEntry> images = new ArrayList<>(numberOfEntries);
+        for (int i = 0; i < 5; i++) {
+            // This copy is important -- we do *not* want to delete files in the test resources directory, and tests might perform file deletion
+            Files.copy(new File(TestUtils.getRegressionDataFile(11685, "2015-11-08_15-33-27-Xiaomi_YI-Y0030832.jpg")).toPath(),
+                    tempDirectory.resolve(i + ".jpg"));
+            images.add(new ImageEntry(tempDirectory.resolve(i + ".jpg").toFile()));
+        }
+        MainApplication.getLayerManager().addLayer(new GeoImageLayer(new ArrayList<>(images), null, "testImageDeletion"));
+        return images;
+    }
+
+    @ParameterizedTest
+    @ValueSource(booleans = {true, false})
+    void testImageDeletion(boolean permanentDeletion) throws IOException, ExecutionException, InterruptedException, TimeoutException {
+        Config.getPref().putBoolean("message.geoimage.deleteimagefromdisk", false);
+        Config.getPref().putInt("message.geoimage.deleteimagefromdisk.value", 2);
+        new ExtendedDialogMocker(); // Just needed to avoid a headless exception.
+        final Action deleteAction;
+        if (permanentDeletion) {
+            deleteAction = ((JButton) ((JPanel) ((JPanel) ((JPanel) this.dialog.getComponent(1)).getComponent(1))
+                    .getComponent(0)).getComponent(9)).getAction();
+            assertEquals("ImageRemoveFromDiskAction", deleteAction.getClass().getSimpleName());
+        } else {
+            deleteAction = ((JButton) ((JPanel) ((JPanel) ((JPanel) this.dialog.getComponent(1)).getComponent(1))
+                    .getComponent(0)).getComponent(8)).getAction();
+            assertEquals("ImageRemoveAction", deleteAction.getClass().getSimpleName());
+        }
+        assertNull(ImageViewerDialog.getCurrentImage());
+        final List<? extends IImageEntry<?>> images = generateImageEntries(5);
+        for (int i = 0; i < 5; i++) {
+            assertSame(images.get(i), ImageViewerDialog.getCurrentImage());
+            deleteAction.actionPerformed(null);
+            assertNotEquals(permanentDeletion, images.get(i).getFile().exists());
+            MainApplication.worker.submit(() -> { /* Sync thread */ }).get(1, TimeUnit.SECONDS);
+        }
+        assertNull(ImageViewerDialog.getCurrentImage());
+    }
+}