diff --git a/apps/builder/app/shared/tailwind/tailwind.test.tsx b/apps/builder/app/shared/tailwind/tailwind.test.tsx
index 5d2b0c7adb3b..f552414de1b7 100644
--- a/apps/builder/app/shared/tailwind/tailwind.test.tsx
+++ b/apps/builder/app/shared/tailwind/tailwind.test.tsx
@@ -114,8 +114,8 @@ test("override border opacity", async () => {
         ws:tag="div"
         ws:style={css`
           border-style: solid;
-          border-width: 1px;
           border-color: rgb(229 231 235 / var(--tw-border-opacity));
+          border-width: 1px;
           --tw-border-opacity: 0.6;
         `}
       ></ws.element>
@@ -315,31 +315,6 @@ describe("extract breakpoints", () => {
     );
   });
 
-  test("base is first breakpoint", async () => {
-    expect(
-      await generateFragmentFromTailwind(
-        renderTemplate(
-          <ws.element
-            ws:tag="div"
-            class="opacity-10 sm:opacity-20"
-          ></ws.element>
-        )
-      )
-    ).toEqual(
-      renderTemplate(
-        <ws.element
-          ws:tag="div"
-          ws:style={css`
-            @media (max-width: 479px) {
-              opacity: 0.1;
-            }
-            opacity: 0.2;
-          `}
-        ></ws.element>
-      )
-    );
-  });
-
   test("base is last breakpoint", async () => {
     expect(
       await generateFragmentFromTailwind(
@@ -393,27 +368,6 @@ describe("extract breakpoints", () => {
     );
   });
 
-  test("preserve breakpoint when no base breakpoint", async () => {
-    expect(
-      await generateFragmentFromTailwind(
-        renderTemplate(
-          <ws.element ws:tag="div" class="sm:opacity-10"></ws.element>
-        )
-      )
-    ).toEqual(
-      renderTemplate(
-        <ws.element
-          ws:tag="div"
-          ws:style={css`
-            @media (min-width: 480px) {
-              opacity: 0.1;
-            }
-          `}
-        ></ws.element>
-      )
-    );
-  });
-
   test("extract container class", async () => {
     expect(
       await generateFragmentFromTailwind(
@@ -427,7 +381,6 @@ describe("extract breakpoints", () => {
             @media (max-width: 479px) {
               max-width: none;
             }
-            width: 100%;
             @media (max-width: 767px) {
               max-width: 640px;
             }
@@ -441,6 +394,7 @@ describe("extract breakpoints", () => {
             @media (min-width: 1440px) {
               max-width: 1536px;
             }
+            width: 100%;
           `}
         ></ws.element>
       )
@@ -501,11 +455,14 @@ describe("extract breakpoints", () => {
           ws:tag="div"
           ws:style={css`
             opacity: 0.1;
-            @media (min-width: 480px) {
+            @media (max-width: 479px) {
               &:hover {
-                opacity: 0.2;
+                opacity: unset;
               }
             }
+            &:hover {
+              opacity: 0.2;
+            }
           `}
         ></ws.element>
       )
@@ -527,21 +484,21 @@ describe("extract breakpoints", () => {
         <ws.element
           ws:tag="div"
           ws:style={css`
-            @media (min-width: 1440px) {
-              opacity: 0.6;
+            @media (max-width: 479px) {
+              opacity: 0.1;
             }
-            @media (min-width: 1280px) {
-              opacity: 0.5;
+            @media (max-width: 767px) {
+              opacity: 0.2;
             }
-            opacity: 0.4;
             @media (max-width: 991px) {
               opacity: 0.3;
             }
-            @media (max-width: 767px) {
-              opacity: 0.2;
+            opacity: 0.4;
+            @media (min-width: 1280px) {
+              opacity: 0.5;
             }
-            @media (max-width: 479px) {
-              opacity: 0.1;
+            @media (min-width: 1440px) {
+              opacity: 0.6;
             }
           `}
         ></ws.element>
@@ -570,6 +527,56 @@ describe("extract breakpoints", () => {
       )
     );
   });
+
+  test("use unset for missing base breakpoint 1", async () => {
+    expect(
+      await generateFragmentFromTailwind(
+        renderTemplate(
+          <ws.element ws:tag="div" class="sm:opacity-10"></ws.element>
+        )
+      )
+    ).toEqual(
+      renderTemplate(
+        <ws.element
+          ws:tag="div"
+          ws:style={css`
+            @media (max-width: 479px) {
+              opacity: unset;
+            }
+            opacity: 0.1;
+          `}
+        ></ws.element>
+      )
+    );
+  });
+
+  test("use unset for missing base breakpoint 2", async () => {
+    expect(
+      await generateFragmentFromTailwind(
+        renderTemplate(
+          <ws.element
+            ws:tag="div"
+            class="max-sm:opacity-10 md:opacity-20"
+          ></ws.element>
+        )
+      )
+    ).toEqual(
+      renderTemplate(
+        <ws.element
+          ws:tag="div"
+          ws:style={css`
+            @media (max-width: 479px) {
+              opacity: 0.1;
+            }
+            @media (max-width: 767px) {
+              opacity: unset;
+            }
+            opacity: 0.2;
+          `}
+        ></ws.element>
+      )
+    );
+  });
 });
 
 test("generate space without display property", async () => {
@@ -635,8 +642,8 @@ test("generate space with display property", async () => {
             @media (max-width: 767px) {
               display: none;
             }
-            row-gap: 1rem;
             display: flex;
+            row-gap: 1rem;
           `}
         ></ws.element>
       </>
diff --git a/apps/builder/app/shared/tailwind/tailwind.ts b/apps/builder/app/shared/tailwind/tailwind.ts
index 834446472262..ded7d3ff3554 100644
--- a/apps/builder/app/shared/tailwind/tailwind.ts
+++ b/apps/builder/app/shared/tailwind/tailwind.ts
@@ -37,23 +37,25 @@ const tailwindToWebstudioMappings: Record<number, undefined | number> = {
   1536: 1440,
 };
 
+type StyleDecl = Omit<ParsedStyleDecl, "selector">;
+
 type Breakpoint = {
-  key: string;
+  styleDecl: StyleDecl;
   minWidth?: number;
   maxWidth?: number;
 };
 
 type Range = {
-  key: string;
+  styleDecl: StyleDecl;
   start: number;
   end: number;
 };
 
 const serializeBreakpoint = (breakpoint: Breakpoint) => {
-  if (breakpoint?.minWidth) {
+  if (breakpoint?.minWidth !== undefined) {
     return `(min-width: ${breakpoint.minWidth}px)`;
   }
-  if (breakpoint?.maxWidth) {
+  if (breakpoint?.maxWidth !== undefined) {
     return `(max-width: ${breakpoint.maxWidth}px)`;
   }
 };
@@ -63,17 +65,17 @@ const UPPER_BOUND = Number.MAX_SAFE_INTEGER;
 const breakpointsToRanges = (breakpoints: Breakpoint[]) => {
   // collect lower bounds and ids
   const values = new Set<number>([0]);
-  const keys = new Map<undefined | number, string>();
+  const styles = new Map<undefined | number, StyleDecl>();
   for (const breakpoint of breakpoints) {
     if (breakpoint.minWidth !== undefined) {
       values.add(breakpoint.minWidth);
-      keys.set(breakpoint.minWidth, breakpoint.key);
+      styles.set(breakpoint.minWidth, breakpoint.styleDecl);
     } else if (breakpoint.maxWidth !== undefined) {
       values.add(breakpoint.maxWidth + 1);
-      keys.set(breakpoint.maxWidth, breakpoint.key);
+      styles.set(breakpoint.maxWidth, breakpoint.styleDecl);
     } else {
       // base breakpoint
-      keys.set(undefined, breakpoint.key);
+      styles.set(undefined, breakpoint.styleDecl);
     }
   }
   const sortedValues = Array.from(values).sort((left, right) => left - right);
@@ -86,9 +88,24 @@ const breakpointsToRanges = (breakpoints: Breakpoint[]) => {
     } else {
       end = sortedValues[index + 1] - 1;
     }
-    const key = keys.get(start) ?? keys.get(end) ?? keys.get(undefined);
-    if (key) {
-      ranges.push({ key, start, end });
+    const styleDecl =
+      styles.get(start) ?? styles.get(end) ?? styles.get(undefined);
+    if (styleDecl) {
+      ranges.push({ styleDecl, start, end });
+      continue;
+    }
+    // when declaration is missing add new one with unset value
+    // to fill the hole in breakpoints
+    // for example
+    // "sm:opacity-20" has a hole at the start
+    // "max-sm:opacity-10 md:opacity-20" has a whole in the middle
+    const example = Array.from(styles.values())[0];
+    if (example) {
+      const newStyleDecl: StyleDecl = {
+        ...example,
+        value: { type: "keyword", value: "unset" },
+      };
+      ranges.push({ styleDecl: newStyleDecl, start, end });
     }
   }
   return ranges;
@@ -96,36 +113,33 @@ const breakpointsToRanges = (breakpoints: Breakpoint[]) => {
 
 const rangesToBreakpoints = (ranges: Range[]) => {
   const breakpoints: Breakpoint[] = [];
-  for (const range of ranges) {
+  for (const { styleDecl, start, end } of ranges) {
     let matchedBreakpoint;
     for (const breakpoint of availableBreakpoints) {
-      if (breakpoint.minWidth === range.start) {
-        matchedBreakpoint = { key: range.key, minWidth: range.start };
+      if (breakpoint.minWidth === start) {
+        matchedBreakpoint = { styleDecl, minWidth: start };
       }
-      if (breakpoint.maxWidth === range.end) {
-        matchedBreakpoint = { key: range.key, maxWidth: range.end };
+      if (breakpoint.maxWidth === end) {
+        matchedBreakpoint = { styleDecl, maxWidth: end };
       }
       if (
         breakpoint.minWidth === undefined &&
         breakpoint.maxWidth === undefined
       ) {
-        matchedBreakpoint ??= { key: range.key };
+        matchedBreakpoint ??= { styleDecl };
       }
     }
     if (matchedBreakpoint) {
+      styleDecl.breakpoint = serializeBreakpoint(matchedBreakpoint);
       breakpoints.push(matchedBreakpoint);
     }
   }
   return breakpoints;
 };
 
-const adaptBreakpoints = (
-  parsedStyles: Omit<ParsedStyleDecl, "selector">[]
-) => {
-  const newStyles: typeof parsedStyles = [];
+const adaptBreakpoints = (parsedStyles: StyleDecl[]) => {
   const breakpointGroups = new Map<string, Breakpoint[]>();
   for (const styleDecl of parsedStyles) {
-    newStyles.push(styleDecl);
     const mediaQuery = styleDecl.breakpoint
       ? parseMediaQuery(styleDecl.breakpoint)
       : undefined;
@@ -143,27 +157,14 @@ const adaptBreakpoints = (
       group = [];
       breakpointGroups.set(groupKey, group);
     }
-    const styleDeclKey = `${styleDecl.breakpoint ?? ""}:${styleDecl.property}:${styleDecl.state ?? ""}`;
-    group.push({ key: styleDeclKey, ...mediaQuery });
+    group.push({ styleDecl, ...mediaQuery });
   }
-  const breakpointsByKey = new Map<string, Breakpoint>();
-  for (let group of breakpointGroups.values()) {
+  const newStyles: typeof parsedStyles = [];
+  for (const group of breakpointGroups.values()) {
     const ranges = breakpointsToRanges(group);
-    // adapt breakpoints only when first range is defined
-    // for example opacity-10 sm:opacity-20 will work
-    // but sm:opacity-20 alone does not have the base to switch to
-    if (ranges[0].start === 0) {
-      group = rangesToBreakpoints(ranges);
-    }
-    for (const breakpoint of group) {
-      breakpointsByKey.set(breakpoint.key, breakpoint);
-    }
-  }
-  for (const styleDecl of newStyles) {
-    const styleDeclKey = `${styleDecl.breakpoint ?? ""}:${styleDecl.property}:${styleDecl.state ?? ""}`;
-    const breakpoint = breakpointsByKey.get(styleDeclKey);
-    if (breakpoint) {
-      styleDecl.breakpoint = serializeBreakpoint(breakpoint);
+    const newGroup = rangesToBreakpoints(ranges);
+    for (const { styleDecl } of newGroup) {
+      newStyles.push(styleDecl);
     }
   }
   return newStyles;
@@ -215,7 +216,7 @@ const parseTailwindClasses = async (classes: string) => {
   const generated = await generator.generate(classes);
   // use tailwind prefix instead of unocss one
   const css = generated.css.replaceAll("--un-", "--tw-");
-  let parsedStyles: Omit<ParsedStyleDecl, "selector">[] = [];
+  let parsedStyles: StyleDecl[] = [];
   // @todo probably builtin in v4
   if (css.includes("border")) {
     // Allow adding a border to an element by just adding a border-width. (https://github.com/tailwindcss/tailwindcss/pull/116)
@@ -264,7 +265,7 @@ const parseTailwindClasses = async (classes: string) => {
       }
     );
   }
-  adaptBreakpoints(parsedStyles);
+  parsedStyles = adaptBreakpoints(parsedStyles);
   const newClasses = classes
     .split(" ")
     .filter((item) => !generated.matched.has(item))
@@ -353,7 +354,7 @@ export const generateFragmentFromTailwind = async (
   };
   const createOrMergeLocalStyles = (
     instanceId: Instance["id"],
-    newStyles: Omit<ParsedStyleDecl, "selector">[]
+    newStyles: StyleDecl[]
   ) => {
     const localStyleSource =
       getLocalStyleSource(instanceId) ?? createLocalStyleSource(instanceId);