AutoLayout link two UILabels to have the same font size

From the UILabel documentation on adjustsFontSizeToWidth:

Normally, the label text is drawn with the font you specify in the font property. If this property is set to YES, however, and the text in the text property exceeds the label’s bounding rectangle, the receiver starts reducing the font size until the string fits or the minimum font size is reached.

I infer from this that the updated font is calculated at drawing time, and the font property is only read, not written to. Therefore, I believe the suggestion by Andrew to use KVO on the font property will not work.

Consequently, to achieve the result you want, you’ll need to calculate the adjusted font size.

As Jackson notes in the comments, this very convenient NSString method to get the actual font has been deprecated in iOS 7. Technically, you could still use it until it’s removed.

Another alternative is to loop through font scales until you find one that will fit both labels. I was able to get it working fine; here’s a sample project that shows how I did it.

Also, here’s the code in case that link ever stops working:

- (void)viewDidLoad
{
    [super viewDidLoad];

    NSLayoutConstraint *constraint = [NSLayoutConstraint constraintWithItem:_rightLabel
                                                                  attribute:NSLayoutAttributeLeft
                                                                  relatedBy:NSLayoutRelationGreaterThanOrEqual
                                                                     toItem:_leftLabel
                                                                  attribute:NSLayoutAttributeRight
                                                                 multiplier:1
                                                                   constant:10];

    [self.view addConstraint:constraint];
}

- (IBAction)makeRightLabelLongerPressed:(id)sender {
    self.rightLabel.text = @"some much longer right label text";
}

- (IBAction)adjustLabelSizes:(id)sender {
    NSLog(@"Attempting to adjust label sizes…");

    CGFloat minimumScaleFactor = fmaxf(self.rightLabel.minimumScaleFactor, self.leftLabel.minimumScaleFactor);;
    UIFont * startingFont = self.rightLabel.font;

    for (double currentScaleFactor = 1.0; currentScaleFactor > minimumScaleFactor; currentScaleFactor -= 0.05) {
        UIFont *font = [startingFont fontWithSize:startingFont.pointSize * currentScaleFactor];
        NSLog(@"  Attempting font with scale %f (size = %f)…", currentScaleFactor, font.pointSize);

        BOOL leftLabelWorks = [self wouldThisFont:font workForThisLabel:self.leftLabel];
        BOOL rightLabelWorks = [self wouldThisFont:font workForThisLabel:self.rightLabel];
        if (leftLabelWorks && rightLabelWorks) {
            NSLog(@"    It fits!");
            self.leftLabel.font = font;
            self.rightLabel.font = font;
            return;
        } else {
            NSLog(@"    It didn't fit. :-(");
        }

    }

    NSLog(@"  It won't fit without violating the minimum scale (%f), so set both to minimum.  Some text may get truncated.", minimumScaleFactor);

    UIFont *minimumFont = [self.rightLabel.font fontWithSize:self.rightLabel.font.pointSize * self.rightLabel.minimumScaleFactor];
    self.rightLabel.font = minimumFont;
    self.leftLabel.font = minimumFont;
}

- (BOOL) wouldThisFont:(UIFont *)testFont workForThisLabel:(UILabel *)testLabel {
    NSDictionary *attributes = [NSDictionary dictionaryWithObjectsAndKeys:testFont, NSFontAttributeName, nil];
    NSAttributedString *as = [[NSAttributedString alloc] initWithString:testLabel.text attributes:attributes];
    CGRect bounds = [as boundingRectWithSize:CGSizeMake(CGRectGetWidth(testLabel.frame), CGFLOAT_MAX) options:(NSStringDrawingUsesLineFragmentOrigin) context:nil];
    BOOL itWorks = [self doesThisSize:bounds.size fitInThisSize:testLabel.bounds.size];
    return itWorks;
}

- (BOOL)doesThisSize:(CGSize)aa fitInThisSize:(CGSize)bb {
    if ( aa.width > bb.width ) return NO;
    if ( aa.height > bb.height ) return NO;
    return YES;
}

This approach could be trivially refactored into a category method that replaces the deprecated method linked to by Jackson.