diff --git a/src/client/application/application-client.vala b/src/client/application/application-client.vala
index 822799bd..ac386e05 100644
--- a/src/client/application/application-client.vala
+++ b/src/client/application/application-client.vala
@@ -366,25 +366,25 @@ public class Application.Client : Gtk.Application {
     }
 
     public override int handle_local_options(GLib.VariantDict options) {
+        int ret = -1;
+        if (options.contains(OPTION_DEBUG)) {
+            Geary.Logging.log_to(GLib.stdout);
+        }
         if (options.contains(OPTION_VERSION)) {
             GLib.stdout.printf(
                 "%s: %s\n", this.binary, Client.VERSION
             );
-            return 0;
+            ret = 0;
         }
-        return -1;
+        return ret;
     }
 
     public override void startup() {
         Environment.set_application_name(NAME);
         Util.International.init(GETTEXT_PACKAGE, this.binary);
+        Util.Date.init();
 
         Configuration.init(this.is_installed, GSETTINGS_DIR);
-        Geary.Logging.init();
-        Geary.Logging.log_to(stderr);
-        GLib.Log.set_writer_func(Geary.Logging.default_log_writer);
-
-        Util.Date.init();
 
         // Add application's actions before chaining up so they are
         // present when the application is first registered on the
@@ -428,7 +428,6 @@ public class Application.Client : Gtk.Application {
             // Since command_line won't be called below if running as
             // a DBus service, disable logging spew and start the
             // controller running.
-            Geary.Logging.log_to(null);
             this.create_controller.begin();
         }
     }
@@ -817,14 +816,6 @@ public class Application.Client : Gtk.Application {
             return 0;
         }
 
-        bool enable_debug = options.contains(OPTION_DEBUG);
-        // Will be logging to stderr until this point
-        if (enable_debug) {
-            Geary.Logging.log_to(GLib.stdout);
-        } else {
-            Geary.Logging.log_to(null);
-        }
-
         bool activated = false;
 
         // Logging flags
@@ -885,7 +876,7 @@ public class Application.Client : Gtk.Application {
             }
         }
 
-        this.config.enable_debug = enable_debug;
+        this.config.enable_debug = options.contains(OPTION_DEBUG);
         this.config.enable_inspector = options.contains(OPTION_INSPECTOR);
         this.config.revoke_certs = options.contains(OPTION_REVOKE_CERTS);
 
diff --git a/src/client/application/main.vala b/src/client/application/main.vala
index c95a3a4c..0df87838 100644
--- a/src/client/application/main.vala
+++ b/src/client/application/main.vala
@@ -25,6 +25,12 @@ int main(string[] args) {
     // proper fix lands. See GNOME/geary#558.
     Environment.set_variable("WEBKIT_USE_SINGLE_WEB_PROCESS", "1", true);
 
+
+    // Init logging right up front so as to capture as many log
+    // messages as possible
+    Geary.Logging.init();
+    GLib.Log.set_writer_func(Geary.Logging.default_log_writer);
+
     Application.Client app = new Application.Client();
 
     int ec = app.run(args);
diff --git a/src/engine/api/geary-logging.vala b/src/engine/api/geary-logging.vala
index 560daf00..bdbe8744 100644
--- a/src/engine/api/geary-logging.vala
+++ b/src/engine/api/geary-logging.vala
@@ -497,15 +497,27 @@ public Record? get_latest_record() {
 }
 
 /**
- * Registers a FileStream to receive all log output from the Engine, be it via the specialized
- * Logging calls (which use the topic-based {@link Flag} or GLib's standard issue
- * debug/message/error/etc. calls ... thus, calling this will also affect the Engine user's calls
- * to those functions.
+ * Registers a FileStream to receive all log output from the engine.
  *
- * If stream is null, no logging occurs.  This is default.
+ * This may be via the specialized Logging calls (which use the
+ * topic-based {@link Flag} or GLib's standard issue
+ * debug/message/error/etc. calls ... thus, calling this will also
+ * affect the Engine user's calls to those functions.
+ *
+ * If stream is null, no logging occurs (the default). If non-null and
+ * the stream was previously null, all pending log records will be
+ * output before proceeding.
  */
 public void log_to(FileStream? stream) {
+    bool catch_up = (stream != null && Logging.stream == null);
     Logging.stream = stream;
+    if (catch_up) {
+        Record? record = Logging.first_record;
+        while (record != null) {
+            write_record(record, record.levels);
+            record = record.next;
+        }
+    }
 }
 
 
@@ -550,6 +562,13 @@ public GLib.LogWriterOutput default_log_writer(GLib.LogLevelFlags levels,
             });
     }
 
+    write_record(record, levels);
+
+    return GLib.LogWriterOutput.HANDLED;
+}
+
+private inline void write_record(Record record,
+                                 GLib.LogLevelFlags levels) {
     // Print a log message to the stream if configured, or if the
     // priority is high enough.
     unowned FileStream? out = stream;
@@ -569,8 +588,6 @@ public GLib.LogWriterOutput default_log_writer(GLib.LogLevelFlags levels,
         out.putc('\n');
         writer_lock.unlock();
     }
-
-    return GLib.LogWriterOutput.HANDLED;
 }