diff --git a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptor.kt b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptor.kt
index 1f6afef7e..3dc9b7229 100644
--- a/amethyst/src/main/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptor.kt
+++ b/amethyst/src/main/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptor.kt
@@ -72,8 +72,13 @@ class LocalBlossomCacheRedirectInterceptor(
     }
 
     private fun findSha256AndExtensionInPath(url: HttpUrl): Triple<Int, String, String>? {
-        url.pathSegments.forEachIndexed { index, segment ->
-            val match = SHA256_SEGMENT_REGEX.find(segment) ?: return@forEachIndexed
+        // Walk segments right-to-left so CDNs that put a cache prefix (itself a
+        // 64-char hex segment) ahead of the blob hash — e.g.
+        // `https://share.yabu.me/<prefix>/<sha>.webp` — still resolve to the
+        // blob and leave the prefix in `xs`.
+        for (index in url.pathSegments.indices.reversed()) {
+            val segment = url.pathSegments[index]
+            val match = SHA256_SEGMENT_REGEX.find(segment) ?: continue
             val sha = match.value.lowercase()
             val ext = guessExtensionFrom(segment, sha) ?: "bin"
             return Triple(index, sha, ext)
diff --git a/amethyst/src/test/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptorTest.kt b/amethyst/src/test/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptorTest.kt
index afaff2dcf..489b1b241 100644
--- a/amethyst/src/test/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptorTest.kt
+++ b/amethyst/src/test/java/com/vitorpamplona/amethyst/service/okhttp/LocalBlossomCacheRedirectInterceptorTest.kt
@@ -132,6 +132,21 @@ class LocalBlossomCacheRedirectInterceptorTest {
         response.close()
     }
 
+    @Test
+    fun bridgeOnPicksRightmostShaWhenPathHasTwoHashes() {
+        // share.yabu.me layout: <cache-prefix-sha>/<blob-sha>.<ext>
+        val prefix = "84b0c46ab699ac35eb2ca286470b85e081db2087cdef63932236c397417782f5"
+        val blob = "28fa4d999af6ae3e4e11bfc2727130ef1b3a13cc0f981e5a93c3996cb2f524e5"
+        val interceptor = LocalBlossomCacheRedirectInterceptor { true }
+        val captured = mutableListOf<String>()
+        val response = interceptor.intercept(fakeChain("https://share.yabu.me/$prefix/$blob.webp", captured))
+        assertEquals(
+            "http://127.0.0.1:24242/$blob.webp?xs=https%3A%2F%2Fshare.yabu.me%2F$prefix",
+            captured.single(),
+        )
+        response.close()
+    }
+
     private fun fakeChain(
         url: String,
         captured: MutableList<String>,
diff --git a/commons/src/commonMain/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExt.kt b/commons/src/commonMain/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExt.kt
index 78d121b6f..6f8d6ce74 100644
--- a/commons/src/commonMain/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExt.kt
+++ b/commons/src/commonMain/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExt.kt
@@ -145,7 +145,10 @@ private fun percentEncode(input: String): String {
 
 private fun extractSha256FromUrlPath(url: String): String? {
     val pathPart = url.substringBefore('?').substringBefore('#')
-    val match = sha256InPathRegex.find(pathPart) ?: return null
+    // Prefer the rightmost 64-char hex segment so CDNs that put a cache prefix
+    // (itself a 64-char hex) ahead of the blob hash — e.g.
+    // `https://share.yabu.me/<prefix>/<sha>.webp` — still resolve to the blob.
+    val match = sha256InPathRegex.findAll(pathPart).lastOrNull() ?: return null
     return match.value.lowercase()
 }
 
@@ -189,7 +192,7 @@ private fun extractServerBase(
     val hostStart = schemeEnd + 3
     if (hostStart >= pathPart.length) return null
 
-    val shaIndex = pathPart.indexOf(sha, ignoreCase = true)
+    val shaIndex = pathPart.lastIndexOf(sha, ignoreCase = true)
     if (shaIndex >= 0) {
         // Anchor on the slash immediately preceding the sha so the cache
         // can append "/<sha>" verbatim per the local-blossom-cache spec.
diff --git a/commons/src/commonTest/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExtTest.kt b/commons/src/commonTest/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExtTest.kt
index db8240220..853dad9b5 100644
--- a/commons/src/commonTest/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExtTest.kt
+++ b/commons/src/commonTest/kotlin/com/vitorpamplona/amethyst/commons/richtext/MediaUrlContentExtTest.kt
@@ -173,4 +173,27 @@ class MediaUrlContentExtTest {
         val uri = "blossom:$sha.jpg?xs=https://nostr.build"
         assertEquals(uri, bridgeProfilePictureUrl(uri, useBridge = true))
     }
+
+    @Test
+    fun bridgeOnPicksRightmostShaWhenPathHasTwoHashes() {
+        // share.yabu.me layout: <cache-prefix-sha>/<blob-sha>.<ext>
+        val prefix = "84b0c46ab699ac35eb2ca286470b85e081db2087cdef63932236c397417782f5"
+        val blob = "28fa4d999af6ae3e4e11bfc2727130ef1b3a13cc0f981e5a93c3996cb2f524e5"
+        val image = MediaUrlImage(url = "https://share.yabu.me/$prefix/$blob.webp", hash = null)
+        assertEquals(
+            "blossom:$blob.webp?xs=https://share.yabu.me/$prefix",
+            image.toCoilModel(useLocalBlossomBridge = true),
+        )
+    }
+
+    @Test
+    fun bridgeProfilePictureUrlPicksRightmostShaWhenPathHasTwoHashes() {
+        val prefix = "84b0c46ab699ac35eb2ca286470b85e081db2087cdef63932236c397417782f5"
+        val blob = "28fa4d999af6ae3e4e11bfc2727130ef1b3a13cc0f981e5a93c3996cb2f524e5"
+        val url = "https://share.yabu.me/$prefix/$blob.webp"
+        assertEquals(
+            "http://127.0.0.1:24242/$blob.webp?xs=https%3A%2F%2Fshare.yabu.me%2F$prefix",
+            bridgeProfilePictureUrl(url, useBridge = true),
+        )
+    }
 }