diff --git a/packages/twenty-front/src/modules/error-handler/components/SentryInitEffect.tsx b/packages/twenty-front/src/modules/error-handler/components/SentryInitEffect.tsx
index 8391f098332..ddd5e44a4a8 100644
--- a/packages/twenty-front/src/modules/error-handler/components/SentryInitEffect.tsx
+++ b/packages/twenty-front/src/modules/error-handler/components/SentryInitEffect.tsx
@@ -29,6 +29,12 @@ export const SentryInitEffect = () => {
         setIsSentryInitializing(true);
 
         try {
+          // oxlint-disable-next-line no-console
+          console.debug(
+            'Initializing Sentry with DSN ending in:',
+            sentryConfig?.dsn?.slice(-8),
+          );
+
           const {
             init,
             browserTracingIntegration,
@@ -59,6 +65,8 @@ export const SentryInitEffect = () => {
             ],
           });
 
+          // oxlint-disable-next-line no-console
+          console.debug('Sentry initialized successfully');
           setIsSentryInitialized(true);
         } catch (error) {
           // oxlint-disable-next-line no-console
@@ -76,6 +84,12 @@ export const SentryInitEffect = () => {
         !isSentryUserDefined
       ) {
         try {
+          // oxlint-disable-next-line no-console
+          console.debug(
+            'Setting Sentry user context for user:',
+            currentUser?.id,
+          );
+
           const { setUser } = await import('@sentry/react');
           setUser({
             email: currentUser?.email,
@@ -83,6 +97,7 @@ export const SentryInitEffect = () => {
             workspaceId: currentWorkspace?.id,
             workspaceMemberId: currentWorkspaceMember?.id,
           });
+
           setIsSentryUserDefined(true);
         } catch (error) {
           // oxlint-disable-next-line no-console
@@ -90,6 +105,9 @@ export const SentryInitEffect = () => {
         }
       } else if (!isDefined(currentUser) && isSentryInitialized) {
         try {
+          // oxlint-disable-next-line no-console
+          console.debug('Clearing Sentry user context');
+
           const { setUser } = await import('@sentry/react');
           setUser(null);
         } catch (error) {
diff --git a/packages/twenty-front/src/modules/file-upload/components/FileUploadProvider.tsx b/packages/twenty-front/src/modules/file-upload/components/FileUploadProvider.tsx
index fc036748e7a..cbc3310d28e 100644
--- a/packages/twenty-front/src/modules/file-upload/components/FileUploadProvider.tsx
+++ b/packages/twenty-front/src/modules/file-upload/components/FileUploadProvider.tsx
@@ -39,11 +39,21 @@ export const FileUploadProvider = ({
 
       try {
         if (!isDefined(files) || files.length === 0) {
+          // oxlint-disable-next-line no-console
+          console.debug('File upload cancelled by user');
           currentOptions.onCancel?.();
         } else {
           const filesArray = Array.from(files);
+          // oxlint-disable-next-line no-console
+          console.debug(
+            `File upload started: ${filesArray.length} file(s) selected`,
+          );
           await currentOptions.onUpload(filesArray);
         }
+      } catch (error) {
+        // oxlint-disable-next-line no-console
+        console.error('File upload error:', error);
+        throw error;
       } finally {
         if (isDefined(fileInputRef.current)) {
           fileInputRef.current.value = '';
@@ -62,7 +72,12 @@ export const FileUploadProvider = ({
     }
 
     try {
+      // oxlint-disable-next-line no-console
+      console.debug('File upload dialog cancelled');
       currentOptions.onCancel?.();
+    } catch (error) {
+      // oxlint-disable-next-line no-console
+      console.error('Error handling file upload cancel:', error);
     } finally {
       if (isDefined(fileInputRef.current)) {
         fileInputRef.current.value = '';