diff --git a/matrix-sdk-android/src/main/java/im/vector/matrix/android/api/auth/data/Versions.kt b/matrix-sdk-android/src/main/java/im/vector/matrix/android/api/auth/data/Versions.kt
index c4186c6ec5..e17209b316 100644
--- a/matrix-sdk-android/src/main/java/im/vector/matrix/android/api/auth/data/Versions.kt
+++ b/matrix-sdk-android/src/main/java/im/vector/matrix/android/api/auth/data/Versions.kt
@@ -18,6 +18,7 @@ package im.vector.matrix.android.api.auth.data
 
 import com.squareup.moshi.Json
 import com.squareup.moshi.JsonClass
+import im.vector.matrix.android.internal.auth.version.HomeServerVersion
 
 /**
  * Model for https://matrix.org/docs/spec/client_server/latest#get-matrix-client-versions
@@ -47,13 +48,13 @@ data class Versions(
 )
 
 // MatrixClientServerAPIVersion
-private const val r0_0_1 = "r0.0.1"
-private const val r0_1_0 = "r0.1.0"
-private const val r0_2_0 = "r0.2.0"
-private const val r0_3_0 = "r0.3.0"
-private const val r0_4_0 = "r0.4.0"
-private const val r0_5_0 = "r0.5.0"
-private const val r0_6_0 = "r0.6.0"
+private val r0_0_1 = HomeServerVersion.parse("r0.0.1")!!
+private val r0_1_0 = HomeServerVersion.parse("r0.1.0")!!
+private val r0_2_0 = HomeServerVersion.parse("r0.2.0")!!
+private val r0_3_0 = HomeServerVersion.parse("r0.3.0")!!
+private val r0_4_0 = HomeServerVersion.parse("r0.4.0")!!
+private val r0_5_0 = HomeServerVersion.parse("r0.5.0")!!
+private val r0_6_0 = HomeServerVersion.parse("r0.6.0")!!
 
 // MatrixVersionsFeature
 private const val FEATURE_LAZY_LOAD_MEMBERS = "m.lazy_load_members"
@@ -83,7 +84,7 @@ fun Versions.isLoginAndRegistrationSupportedBySdk(): Boolean {
  * @return true if the server support the lazy loading of room members
  */
 private fun Versions.supportLazyLoadMembers(): Boolean {
-    return supportedVersions?.contains(r0_5_0) == true
+    return getMaxVersion() >= r0_5_0
             || unstableFeatures?.get(FEATURE_LAZY_LOAD_MEMBERS) == true
 }
 
@@ -92,7 +93,7 @@ private fun Versions.supportLazyLoadMembers(): Boolean {
  * adding a 3pid or resetting password.
  */
 private fun Versions.doesServerRequireIdentityServerParam(): Boolean {
-    if (supportedVersions?.contains(r0_6_0) == true) return false
+    if (getMaxVersion() >= r0_6_0) return false
     return unstableFeatures?.get(FEATURE_REQUIRE_IDENTITY_SERVER) ?: true
 }
 
@@ -101,11 +102,18 @@ private fun Versions.doesServerRequireIdentityServerParam(): Boolean {
  * Some homeservers may trigger errors if they are not prepared for the new parameter.
  */
 private fun Versions.doesServerAcceptIdentityAccessToken(): Boolean {
-    return supportedVersions?.contains(r0_6_0) == true
+    return getMaxVersion() >= r0_6_0
             || unstableFeatures?.get(FEATURE_ID_ACCESS_TOKEN) ?: false
 }
 
 private fun Versions.doesServerSeparatesAddAndBind(): Boolean {
-    return supportedVersions?.contains(r0_6_0) == true
+    return getMaxVersion() >= r0_6_0
             || unstableFeatures?.get(FEATURE_SEPARATE_ADD_AND_BIND) ?: false
 }
+
+private fun Versions.getMaxVersion(): HomeServerVersion {
+    return supportedVersions
+            ?.mapNotNull { HomeServerVersion.parse(it) }
+            ?.max()
+            ?: r0_0_1
+}
diff --git a/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/auth/version/HomeServerVersion.kt b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/auth/version/HomeServerVersion.kt
new file mode 100644
index 0000000000..0ea230774e
--- /dev/null
+++ b/matrix-sdk-android/src/main/java/im/vector/matrix/android/internal/auth/version/HomeServerVersion.kt
@@ -0,0 +1,52 @@
+/*
+ * Copyright (c) 2020 New Vector Ltd
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package im.vector.matrix.android.internal.auth.version
+
+/**
+ * Values will take the form "rX.Y.Z".
+ * Ref: https://matrix.org/docs/spec/client_server/latest#get-matrix-client-versions
+ */
+internal data class HomeServerVersion(
+        val major: Int,
+        val minor: Int,
+        val patch: Int
+) : Comparable<HomeServerVersion> {
+    override fun compareTo(other: HomeServerVersion): Int {
+        return when {
+            major > other.major -> 1
+            major < other.major -> -1
+            minor > other.minor -> 1
+            minor < other.minor -> -1
+            patch > other.patch -> 1
+            patch < other.patch -> -1
+            else                -> 0
+        }
+    }
+
+    companion object {
+        internal val pattern = Regex("""r(\d+)\.(\d+)\.(\d+)""")
+
+        internal fun parse(value: String): HomeServerVersion? {
+            val result = pattern.matchEntire(value) ?: return null
+            return HomeServerVersion(
+                    major = result.groupValues[1].toInt(),
+                    minor = result.groupValues[2].toInt(),
+                    patch = result.groupValues[3].toInt()
+            )
+        }
+    }
+}
diff --git a/matrix-sdk-android/src/test/java/im/vector/matrix/android/api/auth/data/VersionsKtTest.kt b/matrix-sdk-android/src/test/java/im/vector/matrix/android/api/auth/data/VersionsKtTest.kt
new file mode 100644
index 0000000000..b129c019b5
--- /dev/null
+++ b/matrix-sdk-android/src/test/java/im/vector/matrix/android/api/auth/data/VersionsKtTest.kt
@@ -0,0 +1,55 @@
+/*
+ * Copyright (c) 2020 New Vector Ltd
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package im.vector.matrix.android.api.auth.data
+
+import org.amshove.kluent.shouldBe
+import org.junit.Test
+
+class VersionsKtTest {
+
+    @Test
+    fun isSupportedBySdkTooLow() {
+        Versions(supportedVersions = listOf("r0.4.0")).isSupportedBySdk() shouldBe false
+        Versions(supportedVersions = listOf("r0.4.1")).isSupportedBySdk() shouldBe false
+    }
+
+    @Test
+    fun isSupportedBySdkUnstable() {
+        Versions(supportedVersions = listOf("r0.4.0"), unstableFeatures = mapOf("m.lazy_load_members" to true)).isSupportedBySdk() shouldBe true
+    }
+
+    @Test
+    fun isSupportedBySdkOk() {
+        Versions(supportedVersions = listOf("r0.5.0")).isSupportedBySdk() shouldBe true
+        Versions(supportedVersions = listOf("r0.5.1")).isSupportedBySdk() shouldBe true
+    }
+
+    // Was not working
+    @Test
+    fun isSupportedBySdkLater() {
+        Versions(supportedVersions = listOf("r0.6.0")).isSupportedBySdk() shouldBe true
+        Versions(supportedVersions = listOf("r0.6.1")).isSupportedBySdk() shouldBe true
+    }
+
+    // Cover cases of issue #1442
+    @Test
+    fun isSupportedBySdk1442() {
+        Versions(supportedVersions = listOf("r0.5.0", "r0.6.0")).isSupportedBySdk() shouldBe true
+        Versions(supportedVersions = listOf("r0.5.0", "r0.6.1")).isSupportedBySdk() shouldBe true
+        Versions(supportedVersions = listOf("r0.6.0")).isSupportedBySdk() shouldBe true
+    }
+}