diff --git a/src/cli/core/ClassnamesGenerator.ts b/src/cli/core/ClassnamesGenerator.ts
index 9156efad..cb2b02a7 100644
--- a/src/cli/core/ClassnamesGenerator.ts
+++ b/src/cli/core/ClassnamesGenerator.ts
@@ -513,12 +513,26 @@ export class ClassnamesGenerator {
         // If the value is a nested object of color shades...
         if (typeof colorValue === 'object' && colorValue !== null) {
           // Loop over the deep objects and return the result for each key of the object.
-          return Object.keys(colorValue).map(shade => `${utilName}-${colorName}-${shade}`);
+          return Object.keys(colorValue).flatMap(shade => {
+            if (utilName === 'border' && this.isJitModeEnabled()) {
+              return ['', 't', 'r', 'b', 'l'].map(
+                side => `${utilName}-${side}-${colorName}-${shade}`,
+              );
+            } else {
+              return `${utilName}-${colorName}-${shade}`;
+            }
+          });
         }
         // Otherwise...
         else {
           // Return the result of merging the utility name with color value
-          return `${utilName}-${colorName}`;
+          if (utilName === 'border' && this.isJitModeEnabled()) {
+            return ['', 't', 'r', 'b', 'l'].map(
+              side => `${utilName}-${side.length > 0 ? side + '-' : ''}${colorName}`,
+            );
+          } else {
+            return `${utilName}-${colorName}`;
+          }
         }
       });
 
@@ -529,7 +543,7 @@ export class ClassnamesGenerator {
 
     // Return the result classnames based on whether JIT mode is enabled or not
     if (this.isJitModeEnabled()) {
-      return classnamesWithColorsAndOpacitySuffix;
+      return classnamesWithColors.concat(classnamesWithColorsAndOpacitySuffix);
     } else {
       return classnamesWithColors;
     }