diff --git a/apps/app/ui-tests-app/font/all-fonts.ts b/apps/app/ui-tests-app/font/all-fonts.ts
index ef36b0c24..3b4f97260 100644
--- a/apps/app/ui-tests-app/font/all-fonts.ts
+++ b/apps/app/ui-tests-app/font/all-fonts.ts
@@ -6,7 +6,8 @@ import { Label } from "tns-core-modules/ui/label";
 import { FontStyle, FontWeight } from "tns-core-modules/ui/enums";
 import * as typeUtils from "tns-core-modules/utils/types";
 import { Color } from "tns-core-modules/color";
-import * as font from "tns-core-modules/ui/styling/font";
+import * as utils from "tns-core-modules/utils/utils";
+import { isIOS } from "tns-core-modules/platform";
 
 const genericFontFamilies = [
     "system",
@@ -46,18 +47,20 @@ let compareIgnoreCase = function (a, b) {
     return a.toLowerCase().localeCompare(b.toLowerCase());
 };
 
-if (font.ios) {
-    // for (let f = 0; f < embeddedFontNames.length; f++) {
-    //     font.ios.registerFont(`fonts/${embeddedFontNames[f]}.ttf`);
-    // }
+if (isIOS) {
+    const nsFontFamilies = utils.ios.getter(UIFont, UIFont.familyNames);
+    for (let i = 0; i < nsFontFamilies.count; i++) {
+        const family = nsFontFamilies.objectAtIndex(i);
+        fontFamilies.push(family)
 
-    let font_internal = <any>font;
-    font_internal.ensureSystemFontSets();
+        const nsFonts = UIFont.fontNamesForFamilyName(family);
+        for (let j = 0; j < nsFonts.count; j++) {
+            const font = nsFonts.objectAtIndex(j);
+            fontNames.push(font)
+        }
+    }
 
-    (<Set<string>>font_internal.systemFontFamilies).forEach(f => fontFamilies.push(f));
     fontFamilies = fontFamilies.sort(compareIgnoreCase);
-
-    (<Set<string>>font_internal.systemFonts).forEach(f => fontNames.push(f));
     fontNames = fontNames.sort(compareIgnoreCase);
 }
 
@@ -82,8 +85,7 @@ function generateLabels(layout: StackLayout) {
         }
     }
 
-    if (fontFamilies.length > 0)
-    {
+    if (fontFamilies.length > 0) {
         layout.addChild(prepareTitle("Font Families", 24));
     }
     for (let f = 0; f < fontFamilies.length; f++) {
@@ -134,12 +136,12 @@ function prepareLabel(fontFamily: string, fontStyle: string, fontWeight: string)
     let fontStyleCss = fontStyle !== FontStyle.normal ? `font-style: ${fontStyle}; ` : "";
     let fontWeightCss = fontWeight !== FontWeight.normal ? `font-weight: ${fontWeight}; ` : "";
     let css = `${fontFamilyCss}${fontStyleCss}${fontWeightCss}`;
-    label.text = `${typeUtils.getClass(label) } {${css}};`;
+    label.text = `${typeUtils.getClass(label)} {${css}};`;
     label.textWrap = true;
     label.style.textAlignment = "left";
     label.borderWidth = 1;
     label.borderColor = black;
-    label.style.padding = "2"; 
+    label.style.padding = "2";
     label.setInlineStyle(css);
     label.on("loaded", args => {
         let sender = <Label>args.object;
diff --git a/tns-core-modules/ui/styling/font-common.ts b/tns-core-modules/ui/styling/font-common.ts
index ed40bc5df..f06de20a8 100644
--- a/tns-core-modules/ui/styling/font-common.ts
+++ b/tns-core-modules/ui/styling/font-common.ts
@@ -9,8 +9,11 @@ export abstract class FontBase implements FontDefinition {
     }
 
     get isBold(): boolean {
-        return this.fontWeight === FontWeight.BOLD
-            || this.fontWeight === "700";
+        return this.fontWeight === FontWeight.SEMI_BOLD ||
+            this.fontWeight === FontWeight.BOLD ||
+            this.fontWeight === "700" ||
+            this.fontWeight === FontWeight.EXTRA_BOLD ||
+            this.fontWeight === FontWeight.BLACK;
     }
 
     protected constructor(
diff --git a/tns-core-modules/ui/styling/font.android.ts b/tns-core-modules/ui/styling/font.android.ts
index 829b8fbbe..821abad16 100644
--- a/tns-core-modules/ui/styling/font.android.ts
+++ b/tns-core-modules/ui/styling/font.android.ts
@@ -36,15 +36,7 @@ export class Font extends FontBase {
 
     public getAndroidTypeface(): android.graphics.Typeface {
         if (!this._typeface) {
-            let fontStyle = 0;
-            if (this.isBold) {
-                fontStyle |= android.graphics.Typeface.BOLD;
-            }
-            if (this.isItalic) {
-                fontStyle |= android.graphics.Typeface.ITALIC;
-            }
-
-            this._typeface = createTypeface(this, fontStyle);
+            this._typeface = createTypeface(this);
         }
         return this._typeface;
     }
@@ -95,11 +87,19 @@ function loadFontFromFile(fontFamily: string): android.graphics.Typeface {
     return result;
 }
 
-function createTypeface(font: Font, fontStyle: number): android.graphics.Typeface {
+function createTypeface(font: Font): android.graphics.Typeface {
+    let fontStyle = 0;
+    if (font.isBold) {
+        fontStyle |= android.graphics.Typeface.BOLD;
+    }
+    if (font.isItalic) {
+        fontStyle |= android.graphics.Typeface.ITALIC;
+    }
+
     //http://stackoverflow.com/questions/19691530/valid-values-for-androidfontfamily-and-what-they-map-to
     const fonts = parseFontFamily(font.fontFamily);
     let result = null;
-    for (let i = 0; i < fonts.length && !result; i++) {
+    for (let i = 0; i < fonts.length; i++) {
         switch (fonts[i].toLowerCase()) {
             case genericFontFamilies.serif:
                 result = android.graphics.Typeface.create("serif" + getFontWeightSuffix(font.fontWeight), fontStyle);
@@ -116,17 +116,22 @@ function createTypeface(font: Font, fontStyle: number): android.graphics.Typefac
 
             default:
                 result = loadFontFromFile(fonts[i]);
-                if (fontStyle) {
+                if (result && fontStyle) {
                     result = android.graphics.Typeface.create(result, fontStyle);
                 }
                 break;
         }
+
+        if (result) {
+            // Found the font!
+            break;
+        }
     }
 
-    if (fontStyle && !result) {
-        result = android.graphics.Typeface.create(result, fontStyle);
+    if (!result) {
+        result = android.graphics.Typeface.create("sans-serif" + getFontWeightSuffix(font.fontWeight), fontStyle);
     }
-    
+
     return result;
 }
 
diff --git a/tns-core-modules/ui/styling/font.ios.ts b/tns-core-modules/ui/styling/font.ios.ts
index 50c27f517..21c60a67c 100644
--- a/tns-core-modules/ui/styling/font.ios.ts
+++ b/tns-core-modules/ui/styling/font.ios.ts
@@ -1,10 +1,16 @@
 import { FontBase, parseFontFamily, genericFontFamilies, FontStyle, FontWeight } from "./font-common";
 import { isEnabled as traceEnabled, write as traceWrite, categories as traceCategories, messageType as traceMessageType } from "../../trace";
+import { device } from "../../platform"
 import * as fs from "../../file-system";
 import * as utils from "../../utils/utils";
-
 export * from "./font-common";
 
+const EMULATE_OBLIQUE = true;
+const OBLIQUE_TRANSFORM = CGAffineTransformMake(1, 0, 0.2, 1, 0, 0);
+const DEFAULT_SERIF = "Times New Roman";
+const DEFAULT_MONOSPACE = "Courier New";
+const SUPPORT_FONT_WEIGHTS = parseFloat(device.osVersion) >= 10.0;
+
 export class Font extends FontBase {
     public static default = new Font(undefined, undefined, FontStyle.NORMAL, FontWeight.NORMAL);
 
@@ -42,32 +48,6 @@ export class Font extends FontBase {
     }
 }
 
-export const systemFontFamilies = new Set<string>();
-export const systemFonts = new Set<string>();
-
-let areSystemFontSetsValid: boolean = false;
-export function ensureSystemFontSets() {
-    if (areSystemFontSetsValid) {
-        return;
-    }
-
-    const nsFontFamilies = utils.ios.getter(UIFont, UIFont.familyNames);
-    for (let i = 0; i < nsFontFamilies.count; i++) {
-        const family = nsFontFamilies.objectAtIndex(i);
-        systemFontFamilies.add(family);
-
-        const nsFonts = UIFont.fontNamesForFamilyName(family);
-        for (let j = 0; j < nsFonts.count; j++) {
-            const font = nsFonts.objectAtIndex(j);
-            systemFonts.add(font);
-        }
-    }
-    areSystemFontSetsValid = true;
-}
-
-const DEFAULT_SERIF = "Times New Roman";
-const DEFAULT_MONOSPACE = "Courier New";
-
 function getFontFamilyRespectingGenericFonts(fontFamily: string): string {
     if (!fontFamily) {
         return fontFamily;
@@ -85,119 +65,18 @@ function getFontFamilyRespectingGenericFonts(fontFamily: string): string {
     }
 }
 
-function createUIFont(font: Font, defaultFont: UIFont) {
-    let size = font.fontSize || defaultFont.pointSize;
-    let descriptor: UIFontDescriptor;
-
-    let symbolicTraits: number = 0;
-    if (font.isBold) {
-        symbolicTraits |= UIFontDescriptorSymbolicTraits.TraitBold;
-    }
-    if (font.isItalic) {
-        symbolicTraits |= UIFontDescriptorSymbolicTraits.TraitItalic;
-    }
-
-    descriptor = tryResolveWithSystemFont(font, size, symbolicTraits);
-
-    if (!descriptor) {
-        descriptor = tryResolveByFamily(font);
-    }
-
-    if (!descriptor) {
-        descriptor = utils.ios.getter(defaultFont, defaultFont.fontDescriptor).fontDescriptorWithSymbolicTraits(symbolicTraits);
-    }
-
-    return UIFont.fontWithDescriptorSize(descriptor, size);
+function shouldUseSystemFont(fontFamily: string) {
+    return !fontFamily ||
+        fontFamily === genericFontFamilies.sansSerif ||
+        fontFamily === genericFontFamilies.system;
 }
 
-function tryResolveWithSystemFont(font: Font, size: number, symbolicTraits: number): UIFontDescriptor {
-    let systemFont: UIFont;
-    let result: UIFontDescriptor;
-    switch (font.fontFamily) {
-        case genericFontFamilies.sansSerif:
-        case genericFontFamilies.system:
-            if ((<any>UIFont).systemFontOfSizeWeight) {// This method is available on iOS 8.2 and later.
-                systemFont = (<any>UIFont).systemFontOfSizeWeight(size, getiOSFontWeight(font.fontWeight));
-            }
-            else {
-                systemFont = UIFont.systemFontOfSize(size);
-            }
-            result = utils.ios.getter(systemFont, systemFont.fontDescriptor).fontDescriptorWithSymbolicTraits(symbolicTraits);
-            break;
-
-        case genericFontFamilies.monospace:
-            if ((<any>UIFont).monospacedDigitSystemFontOfSizeWeight) {// This method is available on iOS 9.0 and later.
-                systemFont = (<any>UIFont).monospacedDigitSystemFontOfSizeWeight(size, getiOSFontWeight(font.fontWeight));
-                result = utils.ios.getter(systemFont, systemFont.fontDescriptor).fontDescriptorWithSymbolicTraits(symbolicTraits);
-            }
-            break;
-    }
-
-    if (systemFont) {
-        result = utils.ios.getter(systemFont, systemFont.fontDescriptor).fontDescriptorWithSymbolicTraits(symbolicTraits);
-        return result;
-    }
-
-    return null;
-}
-
-function tryResolveByFamily(font: Font): UIFontDescriptor {
-    const fonts = parseFontFamily(font.fontFamily);
-    let result: UIFontDescriptor = null;
-    if (fonts.length === 0) {
-        return null;
-    }
-
-    ensureSystemFontSets();
-
-    for (let i = 0; i < fonts.length; i++) {
-        const fontFamily = getFontFamilyRespectingGenericFonts(fonts[i]);
-        const fontFace = getiOSFontFace(fontFamily, font.fontWeight, font.isItalic);
-        if (systemFonts.has(fontFamily) && !fontFace) { // This is an actual font like `HelveticaNeue-UltraLightItalic` - don't apply font face attribute
-            result = UIFontDescriptor.fontDescriptorWithNameSize(fontFamily, 0);
-        }
-        else if (systemFontFamilies.has(fontFamily)) { // This is a font family like `Helvetica Neue` - apply font face attribute
-            result = createFontDescriptor(fontFamily, fontFace);
-        }
-
-        if (result) {
-            return result;
-        }
-    }
-
-    return null;
-}
-
-function createFontDescriptor(fontFamily: string, fontFace: string): UIFontDescriptor {
-    let fontAttributes = NSMutableDictionary.alloc<string, any>().init();
-    fontAttributes.setObjectForKey(fontFamily, "NSFontFamilyAttribute");
-    if (fontFace) {
-        fontAttributes.setObjectForKey(fontFace, "NSFontFaceAttribute");
-    }
-    return UIFontDescriptor.fontDescriptorWithFontAttributes(fontAttributes);
-}
-
-// Available in iOS 8.2 and later. 
-declare const UIFontWeightThin: number;       //0.8
-declare const UIFontWeightUltraLight: number; //0.6
-declare const UIFontWeightLight: number;      //0.4
-declare const UIFontWeightRegular: number;    //0
-declare const UIFontWeightMedium: number;     //0.23
-declare const UIFontWeightSemibold: number;   //0.3
-declare const UIFontWeightBold: number;       //0.4
-declare const UIFontWeightHeavy: number;      //0.56
-declare const UIFontWeightBlack: number;      //0.62
-
-function getiOSFontWeight(fontWeight: FontWeight): number {
-    if (!(<any>UIFont).systemFontOfSizeWeight) {
-        throw new Error("Font weight is available in iOS 8.2 and later.");
-    }
-
+function getNativeFontWeight(fontWeight: FontWeight): number {
     switch (fontWeight) {
         case FontWeight.THIN:
-            return UIFontWeightThin;
-        case FontWeight.EXTRA_LIGHT:
             return UIFontWeightUltraLight;
+        case FontWeight.EXTRA_LIGHT:
+            return UIFontWeightThin;
         case FontWeight.LIGHT:
             return UIFontWeightLight;
         case FontWeight.NORMAL:
@@ -221,74 +100,78 @@ function getiOSFontWeight(fontWeight: FontWeight): number {
     }
 }
 
-function combineWeightStringWithItalic(weight: string, isItalic: boolean) {
-    if (!isItalic) {
-        return weight;
+function getSystemFont(size: number, nativeWeight: number, italic: boolean, symbolicTraits: number): UIFont {
+    let result = UIFont.systemFontOfSizeWeight(size, nativeWeight);
+    if (italic) {
+        let descriptor = utils.ios.getter(result, result.fontDescriptor).fontDescriptorWithSymbolicTraits(symbolicTraits);
+        result = UIFont.fontWithDescriptorSize(descriptor, size);
     }
 
-    if (!weight) {
-        return "Italic";
+    return result;
+}
+
+function createUIFont(font: Font, defaultFont: UIFont): UIFont {
+    let result: UIFont;
+    const size = font.fontSize || defaultFont.pointSize;
+    const nativeWeight = getNativeFontWeight(font.fontWeight);
+    const fontFamilies = parseFontFamily(font.fontFamily);
+
+    let symbolicTraits: number = 0;
+    if (font.isBold) {
+        symbolicTraits |= UIFontDescriptorSymbolicTraits.TraitBold;
+    }
+    if (font.isItalic) {
+        symbolicTraits |= UIFontDescriptorSymbolicTraits.TraitItalic;
     }
 
-    return weight + " Italic";
-}
+    let fontDescriptorTraits = {
+        [UIFontSymbolicTrait]: symbolicTraits
+    };
 
-function canLoadFont(fontFamily: string, fontFace: string) {
-    const trialDescriptor = createFontDescriptor(fontFamily, fontFace);
-    const trialFont = UIFont.fontWithDescriptorSize(trialDescriptor, 0);
-    return trialFont.familyName === fontFamily;
-}
+    // IOS versions below 10 will not return the correct font when UIFontWeightTrait is set
+    // In this case - rely on UIFontSymbolicTrait only
+    if (SUPPORT_FONT_WEIGHTS) {
+        fontDescriptorTraits[UIFontWeightTrait] = nativeWeight;
+    }
 
-function findCorrectWeightString(fontFamily: string, weightStringAlternatives: Array<string>, isItalic: boolean) {
-    for (let i = 0, length = weightStringAlternatives.length; i < length; i++) {
-        const possibleFontFace = combineWeightStringWithItalic(weightStringAlternatives[i], isItalic);
-        if (canLoadFont(fontFamily, possibleFontFace)) {
-            return weightStringAlternatives[i];
+    for (let i = 0; i < fontFamilies.length; i++) {
+        const fontFamily = getFontFamilyRespectingGenericFonts(fontFamilies[i]);
+
+        if (shouldUseSystemFont(fontFamily)) {
+            result = getSystemFont(size, nativeWeight, font.isItalic, symbolicTraits);
+            break;
+        } else {
+            const fontAttributes = {
+                [UIFontDescriptorFamilyAttribute]: fontFamily,
+                [UIFontDescriptorTraitsAttribute]: fontDescriptorTraits
+            };
+
+            let descriptor = UIFontDescriptor.fontDescriptorWithFontAttributes(<any>fontAttributes);
+            result = UIFont.fontWithDescriptorSize(descriptor, size);
+
+            let actualItalic = utils.ios.getter(result, result.fontDescriptor).symbolicTraits & UIFontDescriptorSymbolicTraits.TraitItalic;
+            if (font.isItalic && !actualItalic && EMULATE_OBLIQUE) {
+                // The font we got is not actually italic so emulate that with a matrix
+                descriptor = descriptor.fontDescriptorWithMatrix(OBLIQUE_TRANSFORM);
+                result = UIFont.fontWithDescriptorSize(descriptor, size);
+            }
+
+            // Check if the resolved font has the correct font-family
+            // If not - fallback to the next font-family
+            if (result.familyName === fontFamily) {
+                break;
+            } else {
+                result = null;
+            }
         }
     }
-    return weightStringAlternatives[0];
-}
 
-function getiOSFontFace(fontFamily: string, fontWeight: FontWeight, isItalic: boolean): string {
-    // ... with a lot of fuzzy logic and artificial intelligence thanks to the lack of font naming standards.
-    let weight: string;
-    switch (fontWeight) {
-        case FontWeight.THIN:
-            weight = "Thin";
-            break;
-        case FontWeight.EXTRA_LIGHT:
-            weight = findCorrectWeightString(fontFamily, ["Ultra Light", "UltraLight", "Extra Light", "ExtraLight", "Ultra light", "Ultralight", "Extra light", "Extralight"], isItalic);
-            break;
-        case FontWeight.LIGHT:
-            weight = "Light";
-            break;
-        case FontWeight.NORMAL:
-        case "400":
-        case undefined:
-        case null:
-            weight = ""; // We dont' need to write Regular
-            break;
-        case FontWeight.MEDIUM:
-            weight = "Medium";
-            break;
-        case FontWeight.SEMI_BOLD:
-            weight = findCorrectWeightString(fontFamily, ["Demi Bold", "DemiBold", "Semi Bold", "SemiBold", "Demi bold", "Demibold", "Semi bold", "Semibold"], isItalic);
-            break;
-        case FontWeight.BOLD:
-        case "700":
-            weight = "Bold";
-            break;
-        case FontWeight.EXTRA_BOLD:
-            weight = findCorrectWeightString(fontFamily, ["Heavy", "Extra Bold", "ExtraBold", "Extra bold", "Extrabold"], isItalic);
-            break;
-        case FontWeight.BLACK:
-            weight = "Black";
-            break;
-        default:
-            throw new Error(`Invalid font weight: "${fontWeight}"`);
+    // Couldn't resolve font - fallback to the system font
+    if (!result) {
+        result = getSystemFont(size, nativeWeight, font.isItalic, symbolicTraits);
     }
 
-    return combineWeightStringWithItalic(weight, isItalic);
+    return result;
 }
 
 export module ios {
@@ -314,8 +197,6 @@ export module ios {
                 traceWrite("Error occur while registering font: " + CFErrorCopyDescription(<NSError>error.value), traceCategories.Error, traceMessageType.error);
             }
         }
-
-        areSystemFontSetsValid = false;
     }
 }
 
@@ -326,7 +207,6 @@ function registerFontsInFolder(fontsFolderPath) {
         if (fs.Folder.exists(fs.path.join(fontsFolderPath, fileEntity.name))) {
             return true;
         }
-
         if (fileEntity instanceof fs.File &&
             ((<fs.File>fileEntity).extension === ".ttf" || (<fs.File>fileEntity).extension === ".otf")) {
             ios.registerFont(fileEntity.name);
@@ -342,5 +222,4 @@ function registerCustomFonts() {
         registerFontsInFolder(fontsDir);
     }
 }
-
 registerCustomFonts();