diff --git a/crates/bitwarden/src/vault/cipher/cipher.rs b/crates/bitwarden/src/vault/cipher/cipher.rs
index 47b58694d..f0138beb9 100644
--- a/crates/bitwarden/src/vault/cipher/cipher.rs
+++ b/crates/bitwarden/src/vault/cipher/cipher.rs
@@ -139,10 +139,15 @@ pub struct CipherListView {
 }
 
 impl KeyEncryptable<SymmetricCryptoKey, Cipher> for CipherView {
-    fn encrypt_with_key(self, key: &SymmetricCryptoKey) -> Result<Cipher, CryptoError> {
+    fn encrypt_with_key(mut self, key: &SymmetricCryptoKey) -> Result<Cipher, CryptoError> {
         let ciphers_key = Cipher::get_cipher_key(key, &self.key)?;
         let key = ciphers_key.as_ref().unwrap_or(key);
 
+        // For compatibility reasons, we only create checksums for ciphers that have a key
+        if ciphers_key.is_some() {
+            self.generate_checksums();
+        }
+
         Ok(Cipher {
             id: self.id,
             organization_id: self.organization_id,
@@ -177,7 +182,7 @@ impl KeyDecryptable<SymmetricCryptoKey, CipherView> for Cipher {
         let ciphers_key = Cipher::get_cipher_key(key, &self.key)?;
         let key = ciphers_key.as_ref().unwrap_or(key);
 
-        Ok(CipherView {
+        let mut cipher = CipherView {
             id: self.id,
             organization_id: self.organization_id,
             folder_id: self.folder_id,
@@ -202,7 +207,14 @@ impl KeyDecryptable<SymmetricCryptoKey, CipherView> for Cipher {
             creation_date: self.creation_date,
             deleted_date: self.deleted_date,
             revision_date: self.revision_date,
-        })
+        };
+
+        // For compatibility we only remove URLs with invalid checksums if the cipher has a key
+        if ciphers_key.is_some() {
+            cipher.remove_invalid_checksums();
+        }
+
+        Ok(cipher)
     }
 }
 
@@ -299,6 +311,20 @@ impl CipherView {
         self.key = Some(new_key.to_vec().encrypt_with_key(key)?);
         Ok(())
     }
+
+    pub fn generate_checksums(&mut self) {
+        if let Some(uris) = self.login.as_mut().and_then(|l| l.uris.as_mut()) {
+            for uri in uris {
+                uri.generate_checksum();
+            }
+        }
+    }
+
+    pub fn remove_invalid_checksums(&mut self) {
+        if let Some(uris) = self.login.as_mut().and_then(|l| l.uris.as_mut()) {
+            uris.retain(|u| u.is_checksum_valid());
+        }
+    }
 }
 
 impl KeyDecryptable<SymmetricCryptoKey, CipherListView> for Cipher {
diff --git a/crates/bitwarden/src/vault/cipher/login.rs b/crates/bitwarden/src/vault/cipher/login.rs
index 5d00c41e1..26fd59001 100644
--- a/crates/bitwarden/src/vault/cipher/login.rs
+++ b/crates/bitwarden/src/vault/cipher/login.rs
@@ -1,3 +1,4 @@
+use base64::{engine::general_purpose::STANDARD, Engine};
 use bitwarden_api_api::models::{CipherLoginModel, CipherLoginUriModel};
 use bitwarden_crypto::{
     CryptoError, EncString, KeyDecryptable, KeyEncryptable, SymmetricCryptoKey,
@@ -28,6 +29,7 @@ pub enum UriMatchType {
 pub struct LoginUri {
     pub uri: Option<EncString>,
     pub r#match: Option<UriMatchType>,
+    pub uri_checksum: Option<EncString>,
 }
 
 #[derive(Serialize, Deserialize, Debug, JsonSchema)]
@@ -36,6 +38,35 @@ pub struct LoginUri {
 pub struct LoginUriView {
     pub uri: Option<String>,
     pub r#match: Option<UriMatchType>,
+    pub uri_checksum: Option<String>,
+}
+
+impl LoginUriView {
+    pub(crate) fn is_checksum_valid(&self) -> bool {
+        let Some(uri) = &self.uri else {
+            return false;
+        };
+        let Some(cs) = &self.uri_checksum else {
+            return false;
+        };
+        let Ok(cs) = STANDARD.decode(cs) else {
+            return false;
+        };
+
+        use sha2::Digest;
+        let uri_hash = sha2::Sha256::new().chain_update(uri.as_bytes()).finalize();
+
+        uri_hash.as_slice() == cs
+    }
+
+    pub(crate) fn generate_checksum(&mut self) {
+        if let Some(uri) = &self.uri {
+            use sha2::Digest;
+            let uri_hash = sha2::Sha256::new().chain_update(uri.as_bytes()).finalize();
+            let uri_hash = STANDARD.encode(uri_hash.as_slice());
+            self.uri_checksum = Some(uri_hash);
+        }
+    }
 }
 
 #[derive(Serialize, Deserialize, Debug, JsonSchema, Clone)]
@@ -93,6 +124,7 @@ impl KeyEncryptable<SymmetricCryptoKey, LoginUri> for LoginUriView {
         Ok(LoginUri {
             uri: self.uri.encrypt_with_key(key)?,
             r#match: self.r#match,
+            uri_checksum: self.uri_checksum.encrypt_with_key(key)?,
         })
     }
 }
@@ -116,6 +148,7 @@ impl KeyDecryptable<SymmetricCryptoKey, LoginUriView> for LoginUri {
         Ok(LoginUriView {
             uri: self.uri.decrypt_with_key(key)?,
             r#match: self.r#match,
+            uri_checksum: self.uri_checksum.decrypt_with_key(key)?,
         })
     }
 }
@@ -166,6 +199,7 @@ impl TryFrom<CipherLoginUriModel> for LoginUri {
         Ok(Self {
             uri: EncString::try_from_optional(uri.uri)?,
             r#match: uri.r#match.map(|m| m.into()),
+            uri_checksum: EncString::try_from_optional(uri.uri_checksum)?,
         })
     }
 }
@@ -208,3 +242,52 @@ impl TryFrom<bitwarden_api_api::models::CipherFido2CredentialModel> for Fido2Cre
         })
     }
 }
+
+#[cfg(test)]
+mod tests {
+    #[test]
+    fn test_valid_checksum() {
+        let uri = super::LoginUriView {
+            uri: Some("https://example.com".to_string()),
+            r#match: Some(super::UriMatchType::Domain),
+            uri_checksum: Some("EAaArVRs5qV39C9S3zO0z9ynVoWeZkuNfeMpsVDQnOk=".to_string()),
+        };
+        assert!(uri.is_checksum_valid());
+    }
+
+    #[test]
+    fn test_invalid_checksum() {
+        let uri = super::LoginUriView {
+            uri: Some("https://example.com".to_string()),
+            r#match: Some(super::UriMatchType::Domain),
+            uri_checksum: Some("UtSgIv8LYfEdOu7yqjF7qXWhmouYGYC8RSr7/ryZg5Q=".to_string()),
+        };
+        assert!(!uri.is_checksum_valid());
+    }
+
+    #[test]
+    fn test_missing_checksum() {
+        let uri = super::LoginUriView {
+            uri: Some("https://example.com".to_string()),
+            r#match: Some(super::UriMatchType::Domain),
+            uri_checksum: None,
+        };
+        assert!(!uri.is_checksum_valid());
+    }
+
+    #[test]
+    fn test_generate_checksum() {
+        let mut uri = super::LoginUriView {
+            uri: Some("https://test.com".to_string()),
+            r#match: Some(super::UriMatchType::Domain),
+            uri_checksum: None,
+        };
+
+        uri.generate_checksum();
+
+        assert_eq!(
+            uri.uri_checksum.unwrap().as_str(),
+            "OWk2vQvwYD1nhLZdA+ltrpBWbDa2JmHyjUEWxRZSS8w="
+        );
+    }
+}