diff --git a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/ImageUploader.kt b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/ImageUploader.kt
index 1e4f4f74e..ccb6b49cb 100644
--- a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/ImageUploader.kt
+++ b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/ImageUploader.kt
@@ -1,60 +1,75 @@
 package com.vitorpamplona.amethyst.ui.actions
 
-import android.graphics.Bitmap
+import android.content.ContentResolver
+import android.net.Uri
 import com.fasterxml.jackson.module.kotlin.jacksonObjectMapper
-import java.io.ByteArrayOutputStream
-import java.io.IOException
-import java.util.UUID
-import okhttp3.Call
-import okhttp3.Callback
+import okhttp3.*
 import okhttp3.MediaType.Companion.toMediaType
-import okhttp3.MultipartBody
-import okhttp3.OkHttpClient
-import okhttp3.Request
-import okhttp3.RequestBody
-import okhttp3.RequestBody.Companion.toRequestBody
-import okhttp3.Response
+import okio.BufferedSink
+import okio.source
+import java.io.IOException
+import java.util.*
 
 object ImageUploader {
-  private fun encodeImage(bitmap: Bitmap): ByteArray {
-    val byteArrayOutPutStream = ByteArrayOutputStream()
-    bitmap.compress(Bitmap.CompressFormat.JPEG, 100, byteArrayOutPutStream)
-    return byteArrayOutPutStream.toByteArray()
-  }
+  fun uploadImage(
+    uri: Uri,
+    contentResolver: ContentResolver,
+    onSuccess: (String) -> Unit,
+    onError: (Throwable) -> Unit,
+) {
+    val contentType = contentResolver.getType(uri)
 
-  fun uploadImage(bitmap: Bitmap, onSuccess: (String) -> Unit) {
     val client = OkHttpClient.Builder().build()
 
-    val body: RequestBody = MultipartBody.Builder()
+    val requestBody: RequestBody = MultipartBody.Builder()
       .setType(MultipartBody.FORM)
       .addFormDataPart(
         "image",
-        "${UUID.randomUUID()}.png",
-        encodeImage(bitmap).toRequestBody("image/png".toMediaType())
+        "${UUID.randomUUID()}",
+        object : RequestBody() {
+          override fun contentType(): MediaType? =
+            contentType?.toMediaType()
+
+          override fun writeTo(sink: BufferedSink) {
+            val imageInputStream = contentResolver.openInputStream(uri)
+            checkNotNull(imageInputStream) {
+              "Can't open the image input stream"
+            }
+
+            imageInputStream.source().use(sink::writeAll)
+          }
+        }
       )
       .build()
 
     val request: Request = Request.Builder()
       .url("https://api.imgur.com/3/image")
       .header("Authorization", "Client-ID e6aea87296f3f96")
-      .post(body)
+      .post(requestBody)
       .build()
 
     client.newCall(request).enqueue(object : Callback {
       override fun onResponse(call: Call, response: Response) {
-        response.use {
-          val body = response.body
-          if (body != null) {
+        try {
+          check(response.isSuccessful)
+          response.body.use { body ->
             val tree = jacksonObjectMapper().readTree(body.string())
             val url = tree?.get("data")?.get("link")?.asText()
-            if (url != null)
-              onSuccess(url)
+            checkNotNull(url) {
+              "There must be an uploaded image URL in the response"
+            }
+
+            onSuccess(url)
           }
+        } catch (e: Exception) {
+          e.printStackTrace()
+          onError(e)
         }
       }
 
       override fun onFailure(call: Call, e: IOException) {
         e.printStackTrace()
+        onError(e)
       }
     })
   }
diff --git a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostView.kt b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostView.kt
index e4ae2a48c..169bf826c 100644
--- a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostView.kt
+++ b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostView.kt
@@ -1,27 +1,13 @@
 package com.vitorpamplona.amethyst.ui.actions
 
+import android.widget.Toast
 import androidx.compose.foundation.border
-import androidx.compose.foundation.layout.Arrangement
-import androidx.compose.foundation.layout.Column
-import androidx.compose.foundation.layout.PaddingValues
-import androidx.compose.foundation.layout.Row
-import androidx.compose.foundation.layout.fillMaxHeight
-import androidx.compose.foundation.layout.fillMaxWidth
-import androidx.compose.foundation.layout.padding
-import androidx.compose.foundation.layout.size
+import androidx.compose.foundation.layout.*
 import androidx.compose.foundation.lazy.LazyColumn
 import androidx.compose.foundation.lazy.itemsIndexed
 import androidx.compose.foundation.shape.RoundedCornerShape
 import androidx.compose.foundation.text.KeyboardOptions
-import androidx.compose.material.Button
-import androidx.compose.material.ButtonDefaults
-import androidx.compose.material.Icon
-import androidx.compose.material.LocalTextStyle
-import androidx.compose.material.MaterialTheme
-import androidx.compose.material.OutlinedTextField
-import androidx.compose.material.Surface
-import androidx.compose.material.Text
-import androidx.compose.material.TextFieldDefaults
+import androidx.compose.material.*
 import androidx.compose.runtime.Composable
 import androidx.compose.runtime.LaunchedEffect
 import androidx.compose.runtime.remember
@@ -37,11 +23,9 @@ import androidx.compose.ui.layout.ContentScale
 import androidx.compose.ui.platform.LocalContext
 import androidx.compose.ui.platform.LocalSoftwareKeyboardController
 import androidx.compose.ui.res.painterResource
-import androidx.compose.ui.text.TextStyle
 import androidx.compose.ui.text.input.KeyboardCapitalization
 import androidx.compose.ui.text.style.TextDirection
 import androidx.compose.ui.unit.dp
-import androidx.compose.ui.unit.sp
 import androidx.compose.ui.window.Dialog
 import androidx.compose.ui.window.DialogProperties
 import androidx.lifecycle.viewmodel.compose.viewModel
@@ -49,12 +33,7 @@ import coil.compose.AsyncImage
 import com.vitorpamplona.amethyst.R
 import com.vitorpamplona.amethyst.model.Account
 import com.vitorpamplona.amethyst.model.Note
-import com.vitorpamplona.amethyst.ui.components.UrlPreview
-import com.vitorpamplona.amethyst.ui.components.VideoView
-import com.vitorpamplona.amethyst.ui.components.imageExtension
-import com.vitorpamplona.amethyst.ui.components.isValidURL
-import com.vitorpamplona.amethyst.ui.components.noProtocolUrlValidator
-import com.vitorpamplona.amethyst.ui.components.videoExtension
+import com.vitorpamplona.amethyst.ui.components.*
 import com.vitorpamplona.amethyst.ui.navigation.UploadFromGallery
 import com.vitorpamplona.amethyst.ui.note.ReplyInformation
 import com.vitorpamplona.amethyst.ui.screen.UserLine
@@ -78,6 +57,10 @@ fun NewPostView(onClose: () -> Unit, baseReplyTo: Note? = null, account: Account
     LaunchedEffect(Unit) {
         delay(100)
         focusRequester.requestFocus()
+
+        postViewModel.imageUploadingError.collect { error ->
+            Toast.makeText(context, error, Toast.LENGTH_SHORT).show()
+        }
     }
 
     Dialog(
@@ -106,7 +89,9 @@ fun NewPostView(onClose: () -> Unit, baseReplyTo: Note? = null, account: Account
                         onClose()
                     })
 
-                    UploadFromGallery {
+                    UploadFromGallery(
+                        isUploading = postViewModel.isUploadingImage,
+                    ) {
                         postViewModel.upload(it, context)
                     }
 
@@ -115,7 +100,8 @@ fun NewPostView(onClose: () -> Unit, baseReplyTo: Note? = null, account: Account
                             postViewModel.sendPost()
                             onClose()
                         },
-                        postViewModel.message.text.isNotBlank()
+                        isActive = postViewModel.message.text.isNotBlank()
+                                && !postViewModel.isUploadingImage
                     )
                 }
 
diff --git a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostViewModel.kt b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostViewModel.kt
index 9c151483f..82762eab6 100644
--- a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostViewModel.kt
+++ b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/NewPostViewModel.kt
@@ -1,24 +1,19 @@
 package com.vitorpamplona.amethyst.ui.actions
 
 import android.content.Context
-import android.graphics.ImageDecoder
 import android.net.Uri
-import android.os.Build
-import android.provider.MediaStore
 import androidx.compose.runtime.getValue
 import androidx.compose.runtime.mutableStateOf
 import androidx.compose.runtime.setValue
 import androidx.compose.ui.text.TextRange
 import androidx.compose.ui.text.input.TextFieldValue
 import androidx.lifecycle.ViewModel
-import com.vitorpamplona.amethyst.model.Account
-import com.vitorpamplona.amethyst.model.LocalCache
-import com.vitorpamplona.amethyst.model.Note
-import com.vitorpamplona.amethyst.model.User
-import com.vitorpamplona.amethyst.model.decodePublicKey
-import com.vitorpamplona.amethyst.model.toHexKey
+import androidx.lifecycle.viewModelScope
+import com.vitorpamplona.amethyst.model.*
 import com.vitorpamplona.amethyst.ui.components.isValidURL
 import com.vitorpamplona.amethyst.ui.components.noProtocolUrlValidator
+import kotlinx.coroutines.flow.MutableSharedFlow
+import kotlinx.coroutines.launch
 import nostr.postr.toNpub
 
 class NewPostViewModel: ViewModel() {
@@ -30,6 +25,8 @@ class NewPostViewModel: ViewModel() {
 
     var message by mutableStateOf(TextFieldValue(""))
     var urlPreview by mutableStateOf<String?>(null)
+    var isUploadingImage by mutableStateOf(false)
+    val imageUploadingError = MutableSharedFlow<String?>()
 
     var userSuggestions by mutableStateOf<List<User>>(emptyList())
     var userSuggestionAnchor: TextRange? = null
@@ -104,26 +101,33 @@ class NewPostViewModel: ViewModel() {
 
         message = TextFieldValue("")
         urlPreview = null
+        isUploadingImage = false
     }
 
     fun upload(it: Uri, context: Context) {
-        val img = if (Build.VERSION.SDK_INT < 28) {
-            MediaStore.Images.Media.getBitmap(context.contentResolver, it)
-        } else {
-            ImageDecoder.decodeBitmap(ImageDecoder.createSource(context.contentResolver, it))
-        }
+        isUploadingImage = true
 
-        img?.let {
-            ImageUploader.uploadImage(img) {
-                message = TextFieldValue(message.text + "\n\n" + it)
+        ImageUploader.uploadImage(
+            uri = it,
+            contentResolver = context.contentResolver,
+            onSuccess = { imageUrl ->
+                isUploadingImage = false
+                message = TextFieldValue(message.text + "\n\n" + imageUrl)
                 urlPreview = findUrlInMessage()
+            },
+            onError = {
+                isUploadingImage = false
+                viewModelScope.launch {
+                    imageUploadingError.emit("Failed to upload the image")
+                }
             }
-        }
+        )
     }
 
     fun cancel() {
         message = TextFieldValue("")
         urlPreview = null
+        isUploadingImage = false
     }
 
     fun findUrlInMessage(): String? {
diff --git a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/UploadFromGallery.kt b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/UploadFromGallery.kt
index 64d4bc0ea..2d4237f11 100644
--- a/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/UploadFromGallery.kt
+++ b/app/src/main/java/com/vitorpamplona/amethyst/ui/actions/UploadFromGallery.kt
@@ -9,12 +9,7 @@ import androidx.compose.foundation.layout.Column
 import androidx.compose.foundation.layout.padding
 import androidx.compose.material.Button
 import androidx.compose.material.Text
-import androidx.compose.runtime.Composable
-import androidx.compose.runtime.SideEffect
-import androidx.compose.runtime.getValue
-import androidx.compose.runtime.mutableStateOf
-import androidx.compose.runtime.remember
-import androidx.compose.runtime.setValue
+import androidx.compose.runtime.*
 import androidx.compose.ui.Alignment
 import androidx.compose.ui.Modifier
 import androidx.compose.ui.unit.dp
@@ -24,7 +19,10 @@ import com.google.accompanist.permissions.rememberPermissionState
 
 @OptIn(ExperimentalPermissionsApi::class)
 @Composable
-fun UploadFromGallery(onImageChosen: (Uri) -> Unit) {
+fun UploadFromGallery(
+    isUploading: Boolean,
+    onImageChosen: (Uri) -> Unit,
+) {
     val cameraPermissionState =
         rememberPermissionState(
             if (Build.VERSION.SDK_INT >= Build.VERSION_CODES.TIRAMISU) {
@@ -50,18 +48,30 @@ fun UploadFromGallery(onImageChosen: (Uri) -> Unit) {
                     modifier = Modifier
                         .align(Alignment.TopCenter)
                         .padding(4.dp),
+                    enabled = !isUploading,
                     onClick = {
                         showGallerySelect = true
                     }
                 ) {
-                    Text("Upload Image")
+                    if (!isUploading) {
+                        Text("Upload Image")
+                    } else {
+                        Text("Uploading…")
+                    }
                 }
             }
         }
     } else {
         Column {
-            Button(onClick = { cameraPermissionState.launchPermissionRequest() }) {
-                Text("Upload Image")
+            Button(
+                onClick = { cameraPermissionState.launchPermissionRequest() },
+                enabled = !isUploading,
+            ) {
+                if (!isUploading) {
+                    Text("Upload Image")
+                } else {
+                    Text("Uploading…")
+                }
             }
         }
     }