diff --git a/packages/wallet/src/SingleAddressWallet.ts b/packages/wallet/src/SingleAddressWallet.ts
index 64e152c4b24..4897f94c15a 100644
--- a/packages/wallet/src/SingleAddressWallet.ts
+++ b/packages/wallet/src/SingleAddressWallet.ts
@@ -171,7 +171,6 @@ export class SingleAddressWallet implements ObservableWallet {
     }: SingleAddressWalletDependencies
   ) {
     this.#logger = contextLogger(logger, this.name);
-    this.#logger.debug('Initializing...');
 
     this.#inputSelector = inputSelector;
 
@@ -205,11 +204,14 @@ export class SingleAddressWallet implements ObservableWallet {
           distinctUntilChanged(groupedAddressesEquals),
           tap(
             // derive an address if none available
-            (addresses) =>
-              addresses.length === 0 &&
-              void keyAgent
-                .deriveAddress({ index: 0, type: AddressType.External })
-                .catch(() => this.#logger.error('Failed to derive address'))
+            (addresses) => {
+              if (addresses.length === 0) {
+                this.#logger.debug('No addresses available; deriving one');
+                void keyAgent
+                  .deriveAddress({ index: 0, type: AddressType.External })
+                  .catch(() => this.#logger.error('Failed to derive address'));
+              }
+            }
           ),
           filter((addresses) => addresses.length > 0),
           tap(stores.addresses.set.bind(stores.addresses))
@@ -218,9 +220,13 @@ export class SingleAddressWallet implements ObservableWallet {
     );
 
     this.name = name;
-    const cancel$ = connectionStatusTracker$.pipe(filter((status) => status === ConnectionStatus.down));
+    const cancel$ = connectionStatusTracker$.pipe(
+      tap((status) => (status === ConnectionStatus.up ? 'Connection UP' : 'Connection DOWN')),
+      filter((status) => status === ConnectionStatus.down)
+    );
     this.#tip$ = this.tip$ = new TipTracker({
       connectionStatus$: connectionStatusTracker$,
+      logger: contextLogger(this.#logger, 'tip$'),
       maxPollInterval: maxInterval,
       minPollInterval: pollInterval,
       provider$: coldObservableProvider({
@@ -336,6 +342,7 @@ export class SingleAddressWallet implements ObservableWallet {
       stores.assets
     );
     this.util = createWalletUtil(this);
+    this.#logger.debug('Created');
   }
 
   async getName(): Promise<string> {
diff --git a/packages/wallet/src/services/TipTracker.ts b/packages/wallet/src/services/TipTracker.ts
index 203ee013d3c..15883ec6f63 100644
--- a/packages/wallet/src/services/TipTracker.ts
+++ b/packages/wallet/src/services/TipTracker.ts
@@ -17,8 +17,10 @@ import {
   startWith,
   switchMap,
   takeUntil,
+  tap,
   timeout
 } from 'rxjs';
+import { Logger } from 'ts-log';
 import { Milliseconds } from './types';
 import { SyncStatus } from '../types';
 export interface TipTrackerProps {
@@ -31,6 +33,7 @@ export interface TipTrackerProps {
    */
   minPollInterval: Milliseconds;
   maxPollInterval: Milliseconds;
+  logger: Logger;
 }
 
 export interface TipTrackerInternals {
@@ -42,9 +45,10 @@ const triggerOrInterval$ = <T = unknown>(trigger$: Observable<T>, interval: numb
 
 export class TipTracker extends PersistentDocumentTrackerSubject<Cardano.Tip> {
   #externalTrigger$ = new Subject<void>();
+  #logger: Logger;
 
   constructor(
-    { provider$, minPollInterval, maxPollInterval, store, syncStatus, connectionStatus$ }: TipTrackerProps,
+    { provider$, minPollInterval, maxPollInterval, store, syncStatus, connectionStatus$, logger }: TipTrackerProps,
     { externalTrigger$ = new Subject() }: TipTrackerInternals = {}
   ) {
     super(
@@ -62,20 +66,34 @@ export class TipTracker extends PersistentDocumentTrackerSubject<Cardano.Tip> {
           connectionStatus$
         ]).pipe(
           // Throttle syncing by interval, cancel ongoing request on external trigger
+          tap(([isSettled, connectionStatus]) => {
+            if (connectionStatus === ConnectionStatus.down) {
+              // REVIEW: slightly redundant since connection debug messages are already recorded separately
+              logger.debug('Connection down. Skipping request');
+            } else {
+              logger.debug(isSettled === null ? 'Initial request' : 'Start request');
+            }
+          }),
           exhaustMap(([_, connectionStatus]) =>
             connectionStatus === ConnectionStatus.down ? EMPTY : provider$.pipe(takeUntil(externalTrigger$))
           ),
-          distinctUntilChanged(tipEquals)
+          distinctUntilChanged(tipEquals),
+          tap((tip) => logger.debug('Fetched new tip', tip))
         ),
         // Always immediately restart request on external trigger
-        externalTrigger$.pipe(switchMap(() => provider$))
+        externalTrigger$.pipe(
+          switchMap(() => provider$),
+          tap((tip) => logger.debug('External trigger fetched tip', tip))
+        )
       ).pipe(finalize(() => this.#externalTrigger$.complete())),
       store
     );
     this.#externalTrigger$ = externalTrigger$;
+    this.#logger = logger;
   }
 
   sync() {
+    this.#logger.debug('Manual sync triggered');
     this.#externalTrigger$.next();
   }
 }
diff --git a/packages/wallet/test/services/TipTracker.test.ts b/packages/wallet/test/services/TipTracker.test.ts
index 043419ed8e8..32b915adbb8 100644
--- a/packages/wallet/test/services/TipTracker.test.ts
+++ b/packages/wallet/test/services/TipTracker.test.ts
@@ -4,6 +4,7 @@ import { InMemoryDocumentStore } from '../../src/persistence';
 import { Milliseconds, SyncStatus } from '../../src';
 import { Observable, firstValueFrom, of } from 'rxjs';
 import { createTestScheduler } from '@cardano-sdk/util-dev';
+import { dummyLogger } from 'ts-log';
 
 const stubObservableProvider = <T>(...calls: Observable<T>[]) => {
   let numCall = 0;
@@ -26,6 +27,7 @@ describe('TipTracker', () => {
   const pollInterval: Milliseconds = 1; // delays emission after trigger
   let store: InMemoryDocumentStore<Cardano.Tip>;
   let connectionStatus$: Observable<ConnectionStatus>;
+  const logger = dummyLogger;
 
   beforeEach(() => {
     store = new InMemoryDocumentStore();
@@ -43,6 +45,7 @@ describe('TipTracker', () => {
       );
       const tracker$ = new TipTracker({
         connectionStatus$,
+        logger,
         maxPollInterval: Number.MAX_VALUE,
         minPollInterval: pollInterval,
         provider$,
@@ -63,6 +66,7 @@ describe('TipTracker', () => {
       const provider$ = cold<Cardano.PartialBlockHeader>('|');
       const tracker$ = new TipTracker({
         connectionStatus$: connectionStatusOffOn$,
+        logger,
         maxPollInterval: Number.MAX_VALUE,
         minPollInterval: pollInterval,
         provider$,
@@ -88,6 +92,7 @@ describe('TipTracker', () => {
       );
       const tracker$ = new TipTracker({
         connectionStatus$,
+        logger,
         maxPollInterval: Number.MAX_VALUE,
         minPollInterval: pollInterval,
         provider$,
@@ -110,6 +115,7 @@ describe('TipTracker', () => {
       );
       const tracker$ = new TipTracker({
         connectionStatus$,
+        logger,
         maxPollInterval: 6,
         minPollInterval: pollInterval,
         provider$,
@@ -132,6 +138,7 @@ describe('TipTracker', () => {
       const provider$ = stubObservableProvider<Cardano.Tip>(cold('x|', mockTips), cold('a|', mockTips));
       const tracker$ = new TipTracker({
         connectionStatus$: connectionStatusMock$,
+        logger,
         maxPollInterval: Number.MAX_VALUE,
         minPollInterval: 0,
         provider$,
@@ -149,6 +156,7 @@ describe('TipTracker', () => {
       const provider$ = cold('x|', mockTips);
       const tracker$ = new TipTracker({
         connectionStatus$: connectionStatusMock$,
+        logger,
         maxPollInterval: 6,
         minPollInterval: 0,
         provider$,