diff --git a/pkg/common/sql_helpers.go b/pkg/common/sql_helpers.go
index 8d62168..5b14ce5 100644
--- a/pkg/common/sql_helpers.go
+++ b/pkg/common/sql_helpers.go
@@ -2,6 +2,7 @@ package common
 
 import (
 	"fmt"
+	"regexp"
 	"strings"
 
 	"github.com/bitechdev/ResolveSpec/pkg/logger"
@@ -207,6 +208,20 @@ func SanitizeWhereClause(where string, tableName string, options ...*RequestOpti
 					}
 				}
 			}
+		} else if tableName != "" && !hasTablePrefix(condToCheck) {
+			// If tableName is provided and the condition DOESN'T have a table prefix,
+			// qualify unambiguous column references to prevent "ambiguous column" errors
+			// when there are multiple joins on the same table (e.g., recursive preloads)
+			columnName := extractUnqualifiedColumnName(condToCheck)
+			if columnName != "" && (validColumns == nil || isValidColumn(columnName, validColumns)) {
+				// Qualify the column with the table name
+				// Be careful to only replace the column name, not other occurrences of the string
+				oldRef := columnName
+				newRef := tableName + "." + columnName
+				// Use word boundary matching to avoid replacing partial matches
+				cond = qualifyColumnInCondition(cond, oldRef, newRef)
+				logger.Debug("Qualified unqualified column in condition: '%s' added table prefix '%s'", oldRef, tableName)
+			}
 		}
 
 		validConditions = append(validConditions, cond)
@@ -483,6 +498,86 @@ func extractTableAndColumn(cond string) (table string, column string) {
 	return "", ""
 }
 
+// extractUnqualifiedColumnName extracts the column name from an unqualified condition
+// For example: "rid_parentmastertaskitem is null" returns "rid_parentmastertaskitem"
+// "status = 'active'" returns "status"
+func extractUnqualifiedColumnName(cond string) string {
+	// Common SQL operators
+	operators := []string{" = ", " != ", " <> ", " > ", " >= ", " < ", " <= ", " LIKE ", " like ", " IN ", " in ", " IS ", " is ", " NOT ", " not "}
+
+	// Find the column reference (left side of the operator)
+	minIdx := -1
+	for _, op := range operators {
+		idx := strings.Index(cond, op)
+		if idx > 0 && (minIdx == -1 || idx < minIdx) {
+			minIdx = idx
+		}
+	}
+
+	var columnRef string
+	if minIdx > 0 {
+		columnRef = strings.TrimSpace(cond[:minIdx])
+	} else {
+		// No operator found, might be a single column reference
+		parts := strings.Fields(cond)
+		if len(parts) > 0 {
+			columnRef = parts[0]
+		}
+	}
+
+	if columnRef == "" {
+		return ""
+	}
+
+	// Remove any quotes
+	columnRef = strings.Trim(columnRef, "`\"'")
+
+	// Return empty if it contains a dot (already qualified) or function call
+	if strings.Contains(columnRef, ".") || strings.Contains(columnRef, "(") {
+		return ""
+	}
+
+	return columnRef
+}
+
+// qualifyColumnInCondition replaces an unqualified column name with a qualified one in a condition
+// Uses word boundaries to avoid partial matches
+// For example: qualifyColumnInCondition("rid_item is null", "rid_item", "table.rid_item")
+// returns "table.rid_item is null"
+func qualifyColumnInCondition(cond, oldRef, newRef string) string {
+	// Use word boundary matching with Go's supported regex syntax
+	// \b matches word boundaries
+	escapedOld := regexp.QuoteMeta(oldRef)
+	pattern := `\b` + escapedOld + `\b`
+
+	re, err := regexp.Compile(pattern)
+	if err != nil {
+		// If regex fails, fall back to simple string replacement
+		logger.Debug("Failed to compile regex for column qualification, using simple replace: %v", err)
+		return strings.Replace(cond, oldRef, newRef, 1)
+	}
+
+	// Only replace if the match is not preceded by a dot (to avoid replacing already qualified columns)
+	result := cond
+	matches := re.FindAllStringIndex(cond, -1)
+
+	// Process matches in reverse order to maintain correct indices
+	for i := len(matches) - 1; i >= 0; i-- {
+		match := matches[i]
+		start := match[0]
+
+		// Check if preceded by a dot (already qualified)
+		if start > 0 && cond[start-1] == '.' {
+			continue
+		}
+
+		// Replace this occurrence
+		result = result[:start] + newRef + result[match[1]:]
+	}
+
+	return result
+}
+
 // findOperatorOutsideParentheses finds the first occurrence of an operator outside of parentheses
 // Returns the index of the operator, or -1 if not found or only found inside parentheses
 func findOperatorOutsideParentheses(s string, operator string) int {
diff --git a/pkg/common/sql_helpers_test.go b/pkg/common/sql_helpers_test.go
index 2874c19..e7cefd4 100644
--- a/pkg/common/sql_helpers_test.go
+++ b/pkg/common/sql_helpers_test.go
@@ -33,16 +33,16 @@ func TestSanitizeWhereClause(t *testing.T) {
 			expected:  "",
 		},
 		{
-			name:      "valid condition with parentheses - no prefix added",
+			name:      "valid condition with parentheses - prefix added to prevent ambiguity",
 			where:     "(status = 'active')",
 			tableName: "users",
-			expected:  "status = 'active'",
+			expected:  "users.status = 'active'",
 		},
 		{
-			name:      "mixed trivial and valid conditions - no prefix added",
+			name:      "mixed trivial and valid conditions - prefix added",
 			where:     "true AND status = 'active' AND 1=1",
 			tableName: "users",
-			expected:  "status = 'active'",
+			expected:  "users.status = 'active'",
 		},
 		{
 			name:      "condition with correct table prefix - unchanged",
@@ -63,10 +63,10 @@ func TestSanitizeWhereClause(t *testing.T) {
 			expected:  "users.status = 'active' AND users.age > 18",
 		},
 		{
-			name:      "multiple valid conditions without prefix - no prefix added",
+			name:      "multiple valid conditions without prefix - prefixes added",
 			where:     "status = 'active' AND age > 18",
 			tableName: "users",
-			expected:  "status = 'active' AND age > 18",
+			expected:  "users.status = 'active' AND users.age > 18",
 		},
 		{
 			name:      "no table name provided",
@@ -90,13 +90,13 @@ func TestSanitizeWhereClause(t *testing.T) {
 			name:      "mixed case AND operators",
 			where:     "status = 'active' AND age > 18 and name = 'John'",
 			tableName: "users",
-			expected:  "status = 'active' AND age > 18 AND name = 'John'",
+			expected:  "users.status = 'active' AND users.age > 18 AND users.name = 'John'",
 		},
 		{
 			name:      "subquery with ORDER BY and LIMIT - allowed",
 			where:     "id IN (SELECT id FROM users WHERE status = 'active' ORDER BY created_at DESC LIMIT 10)",
 			tableName: "users",
-			expected:  "id IN (SELECT id FROM users WHERE status = 'active' ORDER BY created_at DESC LIMIT 10)",
+			expected:  "users.id IN (SELECT users.id FROM users WHERE status = 'active' ORDER BY created_at DESC LIMIT 10)",
 		},
 		{
 			name:      "dangerous DELETE keyword - blocked",
diff --git a/pkg/restheadspec/handler.go b/pkg/restheadspec/handler.go
index 5b55730..55b3fcb 100644
--- a/pkg/restheadspec/handler.go
+++ b/pkg/restheadspec/handler.go
@@ -746,9 +746,29 @@ func (h *Handler) applyPreloadWithRecursion(query common.SelectQuery, preload co
 
 			// Apply ComputedQL fields if any
 			if len(preload.ComputedQL) > 0 {
+				// Get the base table name from the related model
+				baseTableName := getTableNameFromModel(relatedModel)
+				// Convert the preload relation path to the Bun alias format
+				preloadAlias := relationPathToBunAlias(preload.Relation)
+
+				logger.Debug("Applying computed columns to preload %s (alias: %s, base table: %s)",
+					preload.Relation, preloadAlias, baseTableName)
+
 				for colName, colExpr := range preload.ComputedQL {
+					// Replace table references in the expression with the preload alias
+					// This fixes the ambiguous column reference issue when there are multiple
+					// levels of recursive/nested preloads
+					adjustedExpr := colExpr
+					if baseTableName != "" && preloadAlias != "" {
+						adjustedExpr = replaceTableReferencesInSQL(colExpr, baseTableName, preloadAlias)
+						if adjustedExpr != colExpr {
+							logger.Debug("Adjusted computed column expression for %s: '%s' -> '%s'",
+								colName, colExpr, adjustedExpr)
+						}
+					}
+
 					logger.Debug("Applying computed column to preload %s: %s", preload.Relation, colName)
-					sq = sq.ColumnExpr(fmt.Sprintf("(%s) AS %s", colExpr, colName))
+					sq = sq.ColumnExpr(fmt.Sprintf("(%s) AS %s", adjustedExpr, colName))
 					// Remove the computed column from selected columns to avoid duplication
 					for colIndex := range preload.Columns {
 						if preload.Columns[colIndex] == colName {
@@ -841,6 +861,73 @@ func (h *Handler) applyPreloadWithRecursion(query common.SelectQuery, preload co
 	return query
 }
 
+// relationPathToBunAlias converts a relation path like "MAL.MAL.DEF" to the Bun alias format "mal__mal__def"
+// Bun generates aliases for nested relations by lowercasing and replacing dots with double underscores
+func relationPathToBunAlias(relationPath string) string {
+	if relationPath == "" {
+		return ""
+	}
+	// Convert to lowercase and replace dots with double underscores
+	alias := strings.ToLower(relationPath)
+	alias = strings.ReplaceAll(alias, ".", "__")
+	return alias
+}
+
+// replaceTableReferencesInSQL replaces references to a base table name in a SQL expression
+// with the appropriate alias for the current preload level
+// For example, if baseTableName is "mastertaskitem" and targetAlias is "mal__mal",
+// it will replace "mastertaskitem.rid_mastertaskitem" with "mal__mal.rid_mastertaskitem"
+func replaceTableReferencesInSQL(sqlExpr, baseTableName, targetAlias string) string {
+	if sqlExpr == "" || baseTableName == "" || targetAlias == "" {
+		return sqlExpr
+	}
+
+	// Replace both quoted and unquoted table references
+	// Handle patterns like: tablename.column, "tablename".column, tablename."column", "tablename"."column"
+
+	// Pattern 1: tablename.column (unquoted)
+	result := strings.ReplaceAll(sqlExpr, baseTableName+".", targetAlias+".")
+
+	// Pattern 2: "tablename".column or "tablename"."column" (quoted table name)
+	result = strings.ReplaceAll(result, "\""+baseTableName+"\".", "\""+targetAlias+"\".")
+
+	return result
+}
+
+// getTableNameFromModel extracts the table name from a model
+// It checks the bun tag first, then falls back to converting the struct name to snake_case
+func getTableNameFromModel(model interface{}) string {
+	if model == nil {
+		return ""
+	}
+
+	modelType := reflect.TypeOf(model)
+
+	// Unwrap pointers
+	for modelType != nil && modelType.Kind() == reflect.Ptr {
+		modelType = modelType.Elem()
+	}
+
+	if modelType == nil || modelType.Kind() != reflect.Struct {
+		return ""
+	}
+
+	// Look for bun tag on embedded BaseModel
+	for i := 0; i < modelType.NumField(); i++ {
+		field := modelType.Field(i)
+		if field.Anonymous {
+			bunTag := field.Tag.Get("bun")
+			if strings.HasPrefix(bunTag, "table:") {
+				return strings.TrimPrefix(bunTag, "table:")
+			}
+		}
+	}
+
+	// Fallback: convert struct name to lowercase (simple heuristic)
+	// This handles cases like "MasterTaskItem" -> "mastertaskitem"
+	return strings.ToLower(modelType.Name())
+}
+
 func (h *Handler) handleCreate(ctx context.Context, w common.ResponseWriter, data interface{}, options ExtendedRequestOptions) {
 	// Capture panics and return error response
 	defer func() {