diff --git a/flow/cmd/handler.go b/flow/cmd/handler.go
index 99c25cbd28..cf86e97f57 100644
--- a/flow/cmd/handler.go
+++ b/flow/cmd/handler.go
@@ -503,12 +503,12 @@ func (h *FlowRequestHandler) ValidatePeer(
 		}, nil
 	}
 
-	status := conn.ConnectionActive()
-	if !status {
+	_, connErr := conn.ConnectionActive()
+	if connErr != nil {
 		return &protos.ValidatePeerResponse{
 			Status: protos.ValidatePeerStatus_INVALID,
-			Message: fmt.Sprintf("failed to establish active connection to %s peer %s.",
-				req.Peer.Type, req.Peer.Name),
+			Message: fmt.Sprintf("failed to establish active connection to %s peer %s: %v",
+				req.Peer.Type, req.Peer.Name, connErr),
 		}, nil
 	}
 
diff --git a/flow/connectors/bigquery/bigquery.go b/flow/connectors/bigquery/bigquery.go
index 3e33dd3853..f1ee54f4f2 100644
--- a/flow/connectors/bigquery/bigquery.go
+++ b/flow/connectors/bigquery/bigquery.go
@@ -204,13 +204,13 @@ func (c *BigQueryConnector) Close() error {
 }
 
 // ConnectionActive returns true if the connection is active.
-func (c *BigQueryConnector) ConnectionActive() bool {
+func (c *BigQueryConnector) ConnectionActive() (bool, error) {
 	_, err := c.client.Dataset(c.datasetID).Metadata(c.ctx)
 	if err != nil {
-		return false
+		return false, fmt.Errorf("failed to get dataset metadata: %v", err)
 	}
 
-	return c.client != nil
+	return c.client != nil, fmt.Errorf("BigQuery client is nil")
 }
 
 // NeedsSetupMetadataTables returns true if the metadata tables need to be set up.
diff --git a/flow/connectors/core.go b/flow/connectors/core.go
index f39e8f397f..c87869509e 100644
--- a/flow/connectors/core.go
+++ b/flow/connectors/core.go
@@ -21,7 +21,7 @@ var ErrUnsupportedFunctionality = errors.New("requested connector does not suppo
 
 type Connector interface {
 	Close() error
-	ConnectionActive() bool
+	ConnectionActive() (bool, error)
 }
 
 type CDCPullConnector interface {
diff --git a/flow/connectors/eventhub/eventhub.go b/flow/connectors/eventhub/eventhub.go
index 73c8ed528c..ed91314885 100644
--- a/flow/connectors/eventhub/eventhub.go
+++ b/flow/connectors/eventhub/eventhub.go
@@ -65,8 +65,8 @@ func (c *EventHubConnector) Close() error {
 	return allErrors
 }
 
-func (c *EventHubConnector) ConnectionActive() bool {
-	return true
+func (c *EventHubConnector) ConnectionActive() (bool, error) {
+	return true, nil
 }
 
 func (c *EventHubConnector) InitializeTableSchema(req map[string]*protos.TableSchema) error {
diff --git a/flow/connectors/postgres/postgres.go b/flow/connectors/postgres/postgres.go
index e46c383d4c..f411f3ca2e 100644
--- a/flow/connectors/postgres/postgres.go
+++ b/flow/connectors/postgres/postgres.go
@@ -104,11 +104,12 @@ func (c *PostgresConnector) Close() error {
 }
 
 // ConnectionActive returns true if the connection is active.
-func (c *PostgresConnector) ConnectionActive() bool {
+func (c *PostgresConnector) ConnectionActive() (bool, error) {
 	if c.pool == nil {
-		return false
+		return false, fmt.Errorf("connection pool is nil")
 	}
-	return c.pool.Ping(c.ctx) == nil
+	pingErr := c.pool.Ping(c.ctx)
+	return pingErr == nil, pingErr
 }
 
 // NeedsSetupMetadataTables returns true if the metadata tables need to be set up.
diff --git a/flow/connectors/s3/s3.go b/flow/connectors/s3/s3.go
index 1b81cf17df..277c454669 100644
--- a/flow/connectors/s3/s3.go
+++ b/flow/connectors/s3/s3.go
@@ -68,12 +68,6 @@ func NewS3Connector(ctx context.Context,
 		return nil, err
 	}
 
-	validErr := ValidCheck(s3Client, config.Url, pgMetadata)
-	if validErr != nil {
-		log.Errorf("failed to validate s3 connector: %v", validErr)
-		return nil, validErr
-	}
-
 	return &S3Connector{
 		ctx:        ctx,
 		url:        config.Url,
@@ -140,9 +134,19 @@ func ValidCheck(s3Client *s3.S3, bucketURL string, metadataDB *metadataStore.Pos
 	return nil
 }
 
-func (c *S3Connector) ConnectionActive() bool {
+func (c *S3Connector) ConnectionActive() (bool, error) {
 	_, listErr := c.client.ListBuckets(nil)
-	return listErr == nil
+	if listErr != nil {
+		return false, listErr
+	}
+
+	validErr := ValidCheck(&c.client, c.url, c.pgMetadata)
+	if validErr != nil {
+		log.Errorf("failed to validate s3 connector: %v", validErr)
+		return false, validErr
+	}
+
+	return listErr == nil, listErr
 }
 
 func (c *S3Connector) NeedsSetupMetadataTables() bool {
diff --git a/flow/connectors/snowflake/snowflake.go b/flow/connectors/snowflake/snowflake.go
index 08ed4b2d35..7d7c0e934d 100644
--- a/flow/connectors/snowflake/snowflake.go
+++ b/flow/connectors/snowflake/snowflake.go
@@ -168,11 +168,12 @@ func (c *SnowflakeConnector) Close() error {
 	return nil
 }
 
-func (c *SnowflakeConnector) ConnectionActive() bool {
+func (c *SnowflakeConnector) ConnectionActive() (bool, error) {
 	if c == nil || c.database == nil {
-		return false
+		return false, fmt.Errorf("SnowflakeConnector is nil")
 	}
-	return c.database.PingContext(c.ctx) == nil
+	err := c.database.PingContext(c.ctx)
+	return err == nil, err
 }
 
 func (c *SnowflakeConnector) NeedsSetupMetadataTables() bool {
diff --git a/flow/connectors/sql/query_executor.go b/flow/connectors/sql/query_executor.go
index 29291b40ff..02c70c0d22 100644
--- a/flow/connectors/sql/query_executor.go
+++ b/flow/connectors/sql/query_executor.go
@@ -17,7 +17,7 @@ import (
 )
 
 type SQLQueryExecutor interface {
-	ConnectionActive() bool
+	ConnectionActive() (bool, error)
 	Close() error
 
 	CreateSchema(schemaName string) error
diff --git a/flow/connectors/sqlserver/sqlserver.go b/flow/connectors/sqlserver/sqlserver.go
index 5a529c9408..fe75cb74fc 100644
--- a/flow/connectors/sqlserver/sqlserver.go
+++ b/flow/connectors/sqlserver/sqlserver.go
@@ -53,9 +53,9 @@ func (c *SQLServerConnector) Close() error {
 }
 
 // ConnectionActive checks if the connection is still active
-func (c *SQLServerConnector) ConnectionActive() bool {
+func (c *SQLServerConnector) ConnectionActive() (bool, error) {
 	if err := c.db.Ping(); err != nil {
-		return false
+		return false, err
 	}
-	return true
+	return true, nil
 }
diff --git a/flow/e2e/sqlserver/sqlserver_helper.go b/flow/e2e/sqlserver/sqlserver_helper.go
index 1be94fc83e..8c2abba9ec 100644
--- a/flow/e2e/sqlserver/sqlserver_helper.go
+++ b/flow/e2e/sqlserver/sqlserver_helper.go
@@ -41,9 +41,9 @@ func NewSQLServerHelper(name string) (*SQLServerHelper, error) {
 		return nil, err
 	}
 
-	testConn := connector.ConnectionActive()
-	if !testConn {
-		return nil, fmt.Errorf("invalid connection configs")
+	_, connErr := connector.ConnectionActive()
+	if connErr != nil {
+		return nil, fmt.Errorf("invalid connection configs: %v", connErr)
 	}
 
 	rndNum, err := util.RandomUInt64()